So I would like to know what would be my best bet for a conventional loan (heloc/equity loan/etc) and if anyone knows of good lenders for this situation. 

Your best bet might be lowering to $650-675 and trying for a 2-year lease, that way you minimize vacancy next year.And absolutely you should take control of your marketing. 

If I was to bet, I would assume 20 years in the future that tax laws would be less beneficial to investors.

You want to study the ponies, then you might want to create a business around horseracing - I don't know, t-shirts with a picture of a famous stud playing poker or some #hit - rather than betting on one horse to win.

Realistically, your best bet is to find buyers for the 4 properties and charge them  commissions on the deals.

In my experience it depends on zip code, type of property (SFR, duplex, fourplex, more-plex, etc), price of property and amount of down payment - beyond just what you listed.Your best bet is to go to bankrate.com and check there by entering your info.

Your best bet is to find a mentor who expects nothing in return.

You've been buying a long time I bet. 

@Aviv BerkovitchI don't know the Indy market but I'd bet you'd find someone competent for $10-15/hr if you can get them going.Depending on the number of cuts/corners, etc I'd bet you'd be at 1.5 -3.5 days labor to complete a job like this.So, do the math.Of course if you go the 'professional' route IE Homeadvisor be prepared to pay 3-8x that easy.On the paint, I'd probably start my negotiating for that at maybe $650 to $900 depending on number of cuts around trim, etc.Doesn't mean you'd get someone at that but I wouldn't pay more than another 1.2x what I said above.

Bet we’ll be seeing a lot of LLC unwinding happening real soon in the golden state!