I'm looking at a property that is in an HOA that does not allow short-term rentals but wondering if there's like structure I can utilize in order to buy the property and rent it. 

Never had to do this ever before  There are two ways to do this, google and find a template online or get a realtor that can use some promulgated documents by TR.Per law, no-one can write you a legal document except for an attorney or the person providing the document will be infringing the law.In terms of the tenant leaving there is no point to pursue any legal way and for you to get possession, you create a termination notice and then in 30 days you can take possession.

The reality is with a short time horizon there is no cash flow in the DC area.

With my current short term flip loan, I've already worked out a extra 30 day extension if I have to. 

Saw a house with a For Sale by Owner sign in a yard with tall grass and after some drama, we have a house.We have dealt with long term rentals for over 15 years, but not aggressively ( keep them rented and do some improvements ).This "old house" needs, updated HVAC, new roof, new kitchen, some broken windows, upgraded electrical, water run off issues...I'm just starting to clear the house out with multiple dumpsters and starting to get quotes.  

If you flip a house with in a year and incur a tax rate, “ordinary income”then does all of your other income from your rentals “long term income”get taxed at the same rate as ordinary income?

Upfront expenses and monthly payments must be considered when calculating the return on your investment.EXAMPLEI will provide details below, but here's the short version for those who hate to read or do math.

So, long story short.

It is also a great location for short term rentals for multiple reasons including closeness to Yellowstone

We've developed short term property management software based on automations taken from guest messages.