Most of the time a condo/townhome won't be the right fit due to condo fees, hoa fees, etc that make it more costly for the ownership but also more management intensive.

You can always make it the best you can, but a CPA can reclassify it to see how they see fit.

I own another property across the street from the new one so it’s a really good fit.

Learn how to comp correctly and learn how to project rehabs correctly and they become neither good nor bad, just another source of deals for you to underwrite and decide if they fit your buy box. 

Considering your goals, a DSCR loan could be a good fit, with 75% LTV within reach.

For the month to month tenant you can change their lease rate as you see fit… but if you are changing it significantly you should phase it in to help them have time to adjust and prepare for it (in my opinion)… maybe across 2-3 months.It’s likely that your tenants are use to each other having already lived next to each other.  

At worst, and I guarantee MOST fit this group, you get pitched because you just said code for "hi, I'm a paycheck, come and sell me".......If you have 0 focus or intelligent direction for your $$$$, do the smart thing, hire a professional who does and does this as a service. 

I think the biggest issues I've had in the past with other programs is that it's a one size fits all and that's simply not the case.

I'd be willing to meet and see if it's a good fit.

Try to personalize your interactions—get to know your borrowers’ needs and tailor your solutions to fit them.