I am not the most technical person but in this day and age, not being technical is even more reason to welcome opportunities to use platforms that help develop that skill. 

I'm a guy approaching middle-age, living in Chicago.

That has driven a lot of DFW investors to our market but it's still relatively affordable for investors to get started here. 

I'm relatively new to this and am grateful for any advice from the forum. 

Costs will seem high relative to the loan amount on these smaller loans, $5-6k in lender fees isn't uncommon. 

I didn't read the website you were referring to earlier, but I know that there are attorneys who specialize only in dog bite cases - because there are laws on the books that give specific penalties that are non-negotiable, related to dog bites.  

If the loan amount you are looking for is small relative to the value of the first and the second property combined, they are very well secured on a LTV%; ask for a 1% point lower rate.If you don't want to Cross Collateralize, do you have any CD's or MM you can transfer to this bank as collateral. 

In-person behavior can be grounds for rejection, would suggest documenting the behavior and related risk to further protect yourself.

I'd look at the closing docs for something related to the pro-ration of expenses etc and see if you have anything there that could be a clause you point to for them to cover those payments. 

Cash flow, especially in this day and age, should keep the property afloat and paying for itself without you having to put more money into it.