It’s a special property in the small town, and one that a few others have half-heartedly tried to renovate in the past.

There are insurance companies that specialize in short-term rental insurance that covers the home also, and there are insurance companies that offer insurance that provides some coverage for short-term rentals, but typically not as much as one that specializes.For our 3 short-term rentals, we use one of the insurance companies that specialize in STRs because we found they provide better coverage than the standard insurance company. 

@JD Martin is absolutely right - since you've lived in the one unit for 2 out of the previous 5 years the portion of gain attributed to that unit will be tax free. 

Happy to help if you don't have a great lender/LO that specializes in working with real estate investors. 

There are multiple REI specialized tax pros here on the forums.

Perhaps it's a way to reserve capital for future rent specials, but I think in this case you need more information.

Not a lawyer, but one that specializes in this type of law to help you navigate the shifting landscape that is eviction law these days for everyone.  

Special shout out to David Greene!

Check with Proper Insurance https://www.proper.insure/ they specialize in STR insurance

This article will address six important tips that will help you invest wisely.1.DETERMINE IF YOU HAVE THE FINANCIAL MEANS TO INVEST IN RENTAL PROPERTIES2.CONSIDER YOUR GEOGRAPHIC LOCATION AND DESIRED LEVEL OF RISK3.RESEARCH DIFFERENT MARKETS FOR POTENTIAL INVESTMENT OPPORTUNITIES4.GET FINANCING FROM A REPUTABLE LENDER WHO SPECIALIZES IN SINGLE-FAMILY RENTALS 5.FAMILIARIZE YOURSELF WITH THE PROPERTY MANAGEMENT COMPANY THAT YOU ARE GOING TO HIRE6.