If/when tenant does decide to buy it, lets say the total sum between rent credits and purchase option payment was $8,000, you can either take $8,000 off the purchase price or as i would prefer, keep the purchase price but produce a receipt as if the tenant already gave you $8,000 in EMD toward the purchase price so it would count as part of their down payment and make it more manageable for the tenant financially to execute the purchase.

Since I am converting my Primary Residences into a STR MID-YEAR, does that go beyond the personal use days or does it start counting after STR service starts? 

Non-veteran looking to assume a VA loan.Bonus question: If I want to keep and rent out my current residence, is it possible to get potential rent to count towards DTI?

Large unit count and lots of value add opportunity How did you find this deal and how did you negotiate it?

Count me in!

Mind you, you can't count on appreciation, but you can expect at least 2% returns on rentals.

If yours is the only STR within 20 miles and there aren't any cities or larger towns within a 20-30 minute drive, you could easily run into trouble even finding a reliable cleaning person, let alone a full-service STR management company.I would also definitely take the time to find some comps on Airbnb in the same area as yours, with as close to the same bed/bath count as yours, and with the same finishes and amenities as you are planning to put in yours.  

You'll want to get permits because on the property exit you'll be able to count the square footage. 

This is income he is counting on NOW. 

For this reason, it can often be tricky to try to retire, or otherwise count on your cashflow to live off of during the first few years of ownership.