Micah - as Dave mentioned, finding a lender for a HELOC on an investment property can be tough.

Yes that prepay is tough but if you have a ton of equity by then, the equity would be able to pay for the prepay…. not ideal necessarily but it’s an option to not worry too much about that prepay. 

I'm in a tough situation - I have over 100k of equity in my home that I wanted to tap into but I'm in the middle of a remodeling project that will impact an appraisal. 

The south burbs are tough to do business in unless you are in Homewood, Flossmoor, Olympia Fields, or the burbs to the west. 

Quote from @Dave Skow: @Pepper Bradford-  thanks - 1) anyone thats  bringing in  funds for the  down payment on a  inv purchase  will need to be a  co borrower and go on the loan / title   2)  this isnt  anyhting unique or new   for  traditional lenders    3)  many investors  will  balk  at  having to  provide your  lender  all their  financials / tax  returns  etc ....maybe you can  find some that  are OK with this  thats not necessarily true like whats being discussed those with less than 20% interest do not need to PG.. and in the real world your going to have a very tough time getting an investor to put up the equity and ALSO guarantee the debt at that point what do you bring to the table ??

There is a huge supply of rentals on the market now and is tough to raise prices. 

Cleveland is a very tough market to navigate

There’s a reason most of what you are seeing is still in tough parts of those areas.  

DC seems like a tough place to play as a beginner in that case.

The market is tough when the return on cost is less than the interest rate in many areas.