I am wondering what the work around is to purchase properties without it counting towards my DTI.

The insurance company counted all of the labors, such as moving stuff in, moving this out, or prep time.

Fast forward to yesterday(appraisals are done, waiting on underwriting) after a text from the realtor about signing a document that says I'm okay with him representing me and the seller, I called him and brought up the fact that I'd looked over the purchase agreement and the rental agreement and nothing was stated about the rent increase, but it was clearly stated that ALL rental income even prepaid rents (the warehouse was paid in full up front) would be prorated to the buyer (roughly 2200/month)I'm at a crossroads on what to do, part of me wants to just ask for earnest money and appraisal fees back and walk away, but the cashflow of $2300 (current rents not counting warehouse) on a $105,000 property just seems to appealing to walk away from, what do the more experienced investors than myself think

You will learn a lot by doing this.They are probably going to take measurements for flooring and drywall, count any doors that need replaced, look at what appliances need replaced, outlets, fixtures, countertops, etc.

Your gain will be Sales price less sales expenses(Commissions, closing costs) less Adjusted basis.Your Adjusted basis will be Purchase Price plus Improvements less accumulated depreciation.Depending on how you categorized the improvements / furnishings will determine how you will calculate your gain.If you already took depreciation / expenses for the furnishings, you can't also count it towards basis to reduce your gain.Best of luck.

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!