I can PM you a DSCR lender a client of mine has used. 

Will your identified markets be an easy or difficult area to sell once it’s time?

The bank has been extremely difficult to work with up to this point.

Not totally impossible, but at that scale, difficult. 

its even worse in Chicago or in IL as there closing process is so difficult.. they do not have title and escrow in the same place you need and attorney to do this then you need title company to open title and well it aint the west cost were you can get these closed in 48 to 72 hours if you have a great relationship with your Escrow company that is also the title company..

Hi Alex,It's more difficult for sure, but it's doable if you either search enough or make it doable.

So take it one step at a time but definitely make a plan to take that first step as soon as you can.Personally, I like AirBnb/STR's and Fix&Flips for your budget because I have a number of clients who started out in these areas and were able to build up cash and personal wealth faster than the clients who started out with long term rentals.

He's a real estate investor himself and supports a ton of clients in real estate as well.

@Robert MendenhallWe always put a walkthrough contingency on multifamily that our client have under contract. 

My thought is since I would find a single family home into a duplex that has had a very short, or possibly no rental history it could cause trouble at appraisal since NOI would be difficult show.