Investors generally “graduate” to DSCR loans after having a few investment properties under their belt since there are limits on the number of conventional loans that can be used for investment properties, DTI qualification becomes much tougher with a growing portfolio and the hassle and paperwork can become too much when trying to scale aggressively.

My question is for tax purposes, are we hurting ourselves in terms of the qualification of materially participating and maximizing tax deductions on our W2s by purchasing so late in the year? 

There's a new $1m cap that even if you meet all the qualifications and jump through the hoops, there could be some reassessment depending on how much the property has appreciated compared to its assessed value. 

As far as what to look for . . . . ask about the qualifications of the person who is actually going to do the study.

Almost uniformly, a lender is not going to take 6 months an annualize it for an STR, and will only do an actual 12-month history for qualification (this is primarily due to the seasonal nature of most markets, so it would be unrealistic to project if it was the "6 month on season" or "off season". 

But before sending them off to a tour,  I ask if they meet the "pre-qualification requirements".

I can't believe someone with these qualifications would reverse an ACH, trash a home, and stop paying rent.

In addition, I'm suspecting some prospective tenants may be turned off by having to download an app to complete the pre-qualification prior to viewing the property, as others have mentioned here.

So, DSCR loans are conventional loans geared for real estate investors where the proof of income for qualification is not your personal W-2s/1099s or bank statements but rather the monthly rental income vs PITIA expenses(loan pricipal&interest, taxes, insurance, HOA if applicable).This is great because they do not use your income but if the rent will cover these expenses on the property every month.Lenders usually look at the DSCR ratio to decide to lend and the loan pricing too.

Full doc, bank statement and debt service for qualification methods.