If you walked up to Michael Jordan and said, "I want to learn sports" he would walk away.

@Mak K.Your best bet is to get multiple quotes and do research on the roofing companies.

you bet.

.)- DSCR Loans - typically your best bet if you don't quality (or have "outgrown") conventional or looking to scale a portfolio or diving into more specialized markets. 

I think that is your best bet.

If it's unable to be rented, a bridge type loan that Erik mentioned may be best bet.

Otherwise your best bet might be to network in local REIAs with other investors who purchase at tax sales.

. $250K a unit is also somewhat realistic in those submarkets, though not impossible.Your best bet is a value-add strategy on something that has significant upside with a high growth submarket.

To buy a BIG property today, you will need to take on extreme leverage, make a big bet, convince mulitple other people to hand you hundreds of thousands or millions of dollars, and then you have to be right, inside of a 3-5 year timebox, about your projections, supply, demand, expenses, and cap rates. 

As Brie mentioned, you can not deny tenants because of their vouchers.There are other subsidies that you could look into besides CHA.I bet @Mark Ainley or @Jared Kott could provide some better context than me around the subject.