I assume the reason to do this is that the  gain is well above the 121 exclusion.

I will of course be mainly investing in REAL-estate but not completely exclusive.

✓Second Home Requirementsmust be occupied by the borrower for some portion of the yearis restricted to one-unit dwellingsmust be suitable for year-round occupancythe borrower must have exclusive control over the propertymust not be rental property or a timeshare arrangement1cannot be subject to any agreements that give a management firm control over the occupancy of the propertyhttps://selling-guide.fanniema...

Did you have an exclusive buyers agency agreement signed with the agent?

Some of the criteria I use :-Majority of contents and valuables removed -Utilities off-Have neighbors seen any recent activity -Mail or newspapers gathering -Obviously behind on rentThis is an area where you need to use your own judgment and take a risk assessment.

Websites like Craigslist or your local newspaper might have advertisements for people holding garage sales or For Sale By Owners (FSBO) where you can check out a couple on a Saturday as you drive for dollars.

I contract here in Houston exclusively to REI’s because of the volume of work and many times are more careful how they spend their money than they are.Also a lot of new REI’s ask for estimates before they purchase the property and then several hours are wasted for the contractor.

@Chris Klingemann You only get the tax exclusion on your primary home. 

@Chris KlingemannIf it was your primary residence for 2+ years and then an STR for no more than 3 years - then yes, you should qualify for an exclusion, subject to some other restrictions, such as no other residence sold within 2 years, and depreciation recapture tax still applies.If you never lived there yourself, then full capital gain tax due, unless you apply another tax strategy like a 1031 exchange.

Can Itemize deduction.Note: The exclusion for rents when the property is rented for fewer than 15 days only applies to a home that qualifies as a residence.