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Segmented Information (Tables)
 9 Months Ended
Sep. 30, 2018
Segmented Information [Abstract]  
Segment Reporting Disclosure [Text Block]
SEGMENTED INFORMATION
The Company conducts its business through the following two reportable segments: Extended Warranty and Leased Real Estate.
Prior to the second quarter of 2018, the Company conducted its business through a third reportable segment, Insurance Underwriting. Insurance Underwriting included the following subsidiaries of the Company: Mendota, Amigo and Kingsway Reinsurance Corporation ("Kingsway Re"). As further discussed in Note 5, "Acquisition, Disposition and Discontinued Operations," on October 18, 2018, the Company announced that it had completed the sale of Mendota. As a result, Mendota has been classified as discontinued operations and the results of their operations are reported separately for all periods presented. As a result of classifying Mendota as discontinued operations, the composition of the Insurance Underwriting segment has changed such that it no longer meets the criteria of a reportable segment. As such, all segmented information has been restated to exclude the Insurance Underwriting segment for all periods presented.
Extended Warranty Segment
Extended Warranty includes the following subsidiaries of the Company: IWS, Trinity and PWSC (collectively, "Extended Warranty").

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by credit unions in 23 states and the District of Columbia to their members.
Trinity sells HVAC, standby generator, commercial LED lighting and refrigeration warranty products and provides equipment breakdown and maintenance support services to companies across the United States. As a seller of warranty products, Trinity markets and administers product warranty contracts for certain new and used products in the HVAC, standby generator, commercial LED lighting and refrigeration industries throughout the United States. Trinity acts as an agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. Trinity does not guaranty the performance underlying the warranty contracts it sells. As a provider of equipment breakdown and maintenance support services, Trinity acts as a single point of contact to its clients for both certain equipment breakdowns and scheduled maintenance of equipment. Trinity will provide such repair and breakdown services by contracting with certain HVAC providers.
PWSC sells new home warranty products and provides administration services to home builders and homeowners across the United States. PWSC distributes its products and services through an in house sales team and through insurance brokers and insurance carriers throughout all states except Alaska and Louisiana.
Leased Real Estate Segment
Leased Real Estate includes the Company's subsidiary, CMC, which was acquired on July 14, 2016. CMC owns a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property") that is leased to a third party pursuant to a long-term triple net lease. The Real Property is also subject to the Mortgage. When assessing and measuring the operational and financial performance of the Leased Real Estate segment, interest expense related to the Mortgage is included in Leased Real Estate's segment operating income.

Revenues and Operating Income by Reportable Segment
Results for the Company's reportable segments are based on the Company's internal financial reporting systems and are consistent with those followed in the preparation of the unaudited consolidated interim financial statements. The following tables provide financial data used by management. Segment assets are not allocated for management use and, therefore, are not included in the segment disclosures below.
Revenues by reportable segment reconciled to consolidated revenues for the three and nine months ended September 30, 2018 and September 30, 2017 were:
(in thousands)
 
Three months ended September 30,
 
 
Nine months ended September 30,
 
 
 
2018

 
2017

 
2018

 
2017

Revenues:
 
 
 
 
 
 
 
 
Extended Warranty:
 
 
 
 
 
 
 
 
Service fee and commission income
 
$
9,104

 
$
7,670

 
$
28,938

 
$
20,738

Other income
 
34

 
34

 
136

 
170

Total Extended Warranty
 
9,138

 
7,704

 
29,074

 
20,908

Leased Real Estate:
 
 
 
 
 
 
 
 
Rental income
 
3,341

 
3,341

 
10,023

 
10,023

Other income
 
(51
)
 
59

 
168

 
431

Total Leased Real Estate
 
3,290

 
3,400

 
10,191

 
10,454

Total segment revenues
 
12,428

 
11,104

 
39,265

 
31,362

Rental income not allocated to segments
 
—

 
4

 
10

 
18

Net investment (loss) income
 
(84
)
 
1,289

 
(697
)
 
126

Net realized losses
 
(414
)
 
—

 
(405
)
 
(1
)
Gain on change in fair value of equity investments
 
337

 
—

 
951

 
—

Other income not allocated to segments
 
32

 
599

 
1,019

 
660

Total revenues
 
$
12,299

 
$
12,996

 
$
40,143

 
$
32,165


The operating income by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. Total segment operating income reconciled to the consolidated loss from continuing operations for the three and nine months ended September 30, 2018 and September 30, 2017 were:
(in thousands)
 
Three months ended September 30,
 
 
Nine months ended September 30,
 
 
 
2018

 
2017

 
2018

 
2017

Segment operating income:
 
 
 
 
 
 
 
 
Extended Warranty
 
$
385

 
$
847

 
$
3,615

 
$
2,118

Leased Real Estate
 
473

 
525

 
1,965

 
2,315

Total segment operating income
 
858

 
1,372

 
5,580

 
4,433

Net investment (loss) income
 
(84
)
 
1,289

 
(697
)
 
126

Net realized losses
 
(414
)
 
—

 
(405
)
 
(1
)
Gain on change in fair value of equity investments
 
337

 
—

 
951

 
—

Interest expense not allocated to segments
 
(1,571
)
 
(1,261
)
 
(4,476
)
 
(3,636
)
Other income and expenses not allocated to segments, net
 
225

 
(1,872
)
 
(4,428
)
 
(6,871
)
Amortization of intangible assets
 
(1,356
)
 
(286
)
 
(1,899
)
 
(866
)
Contingent consideration benefit
 
—

 
—

 
—

 
212

Loss on change in fair value of debt
 
(1,450
)
 
(1,178
)
 
(2,511
)
 
(5,769
)
Gain on disposal of subsidiary
 
—

 
—

 
17

 
—

Equity in net (loss) income of investee
 
(339
)
 
(897
)
 
(623
)
 
1,343

Loss from continuing operations before income tax (benefit) expense
 
(3,794
)
 
(2,833
)
 
(8,491
)
 
(11,029
)
Income tax (benefit) expense
 
(147
)
 
120

 
291

 
1,636

Loss from continuing operations
 
$
(3,647
)
 
$
(2,953
)
 
$
(8,782
)
 
$
(12,665
)
Reconciliation of Revenue from Segments to Consolidated [Table Text Block]
Revenues by reportable segment reconciled to consolidated revenues for the three and nine months ended September 30, 2018 and September 30, 2017 were:
(in thousands)
 
Three months ended September 30,
 
 
Nine months ended September 30,
 
 
 
2018

 
2017

 
2018

 
2017

Revenues:
 
 
 
 
 
 
 
 
Extended Warranty:
 
 
 
 
 
 
 
 
Service fee and commission income
 
$
9,104

 
$
7,670

 
$
28,938

 
$
20,738

Other income
 
34

 
34

 
136

 
170

Total Extended Warranty
 
9,138

 
7,704

 
29,074

 
20,908

Leased Real Estate:
 
 
 
 
 
 
 
 
Rental income
 
3,341

 
3,341

 
10,023

 
10,023

Other income
 
(51
)
 
59

 
168

 
431

Total Leased Real Estate
 
3,290

 
3,400

 
10,191

 
10,454

Total segment revenues
 
12,428

 
11,104

 
39,265

 
31,362

Rental income not allocated to segments
 
—

 
4

 
10

 
18

Net investment (loss) income
 
(84
)
 
1,289

 
(697
)
 
126

Net realized losses
 
(414
)
 
—

 
(405
)
 
(1
)
Gain on change in fair value of equity investments
 
337

 
—

 
951

 
—

Other income not allocated to segments
 
32

 
599

 
1,019

 
660

Total revenues
 
$
12,299

 
$
12,996

 
$
40,143

 
$
32,165
Reconciliation of Operating Profit (Loss) from Segments to Consolidated [Table Text Block]
egment operating income reconciled to the consolidated loss from continuing operations for the three and nine months ended September 30, 2018 and September 30, 2017 were:
(in thousands)
 
Three months ended September 30,
 
 
Nine months ended September 30,
 
 
 
2018

 
2017

 
2018

 
2017

Segment operating income:
 
 
 
 
 
 
 
 
Extended Warranty
 
$
385

 
$
847

 
$
3,615

 
$
2,118

Leased Real Estate
 
473

 
525

 
1,965

 
2,315

Total segment operating income
 
858

 
1,372

 
5,580

 
4,433

Net investment (loss) income
 
(84
)
 
1,289

 
(697
)
 
126

Net realized losses
 
(414
)
 
—

 
(405
)
 
(1
)
Gain on change in fair value of equity investments
 
337

 
—

 
951

 
—

Interest expense not allocated to segments
 
(1,571
)
 
(1,261
)
 
(4,476
)
 
(3,636
)
Other income and expenses not allocated to segments, net
 
225

 
(1,872
)
 
(4,428
)
 
(6,871
)
Amortization of intangible assets
 
(1,356
)
 
(286
)
 
(1,899
)
 
(866
)
Contingent consideration benefit
 
—

 
—

 
—

 
212

Loss on change in fair value of debt
 
(1,450
)
 
(1,178
)
 
(2,511
)
 
(5,769
)
Gain on disposal of subsidiary
 
—

 
—

 
17

 
—

Equity in net (loss) income of investee
 
(339
)
 
(897
)
 
(623
)
 
1,343

Loss from continuing operations before income tax (benefit) expense
 
(3,794
)
 
(2,833
)
 
(8,491
)
 
(11,029
)
Income tax (benefit) expense
 
(147
)
 
120

 
291

 
1,636

Loss from continuing operations
 
$
(3,647
)
 
$
(2,953
)
 
$
(8,782
)
 
$
(12,665
)
Revenue from External Customers by Geographic Areas [Table Text Block]
(in thousands)
 
Three months ended September 30,
 
 
Nine months ended September 30,
 
 
 
2018

 
2017

 
2018

 
2017

Segment operating income:
 
 
 
 
 
 
 
 
Extended Warranty
 
$
385

 
$
847

 
$
3,615

 
$
2,118

Leased Real Estate
 
473

 
525

 
1,965

 
2,315

Total segment operating income
 
858

 
1,372

 
5,580

 
4,433

Net investment (loss) income
 
(84
)
 
1,289

 
(697
)
 
126

Net realized losses
 
(414
)
 
—

 
(405
)
 
(1
)
Gain on change in fair value of equity investments
 
337

 
—

 
951

 
—

Interest expense not allocated to segments
 
(1,571
)
 
(1,261
)
 
(4,476
)
 
(3,636
)
Other income and expenses not allocated to segments, net
 
225

 
(1,872
)
 
(4,428
)
 
(6,871
)
Amortization of intangible assets
 
(1,356
)
 
(286
)
 
(1,899
)
 
(866
)
Contingent consideration benefit
 
—

 
—

 
—

 
212

Loss on change in fair value of debt
 
(1,450
)
 
(1,178
)
 
(2,511
)
 
(5,769
)
Gain on disposal of subsidiary
 
—

 
—

 
17

 
—

Equity in net (loss) income of investee
 
(339
)
 
(897
)
 
(623
)
 
1,343

Loss from continuing operations before income tax (benefit) expense
 
(3,794
)
 
(2,833
)
 
(8,491
)
 
(11,029
)
Income tax (benefit) expense
 
(147
)
 
120

 
291

 
1,636

Loss from continuing operations
 
$
(3,647
)
 
$
(2,953
)
 
$
(8,782
)
 
$
(12,665
)