I would also recommend seeing if there are any local realtors that you could do an internship with in your area?

I plan to use a HELOC but would be interested in the thoughts of others in BPs on this approach or recommendations if there are other ways to financing that I should consider.

I recommend checking the areas near University Circle for that reason, but there are some spots not far from there that can be rough, so do your due diligence.

Quote from @Andrew Betts: Hi Michael - We own and manage homes in Solara, I can recommend it for a strong ROI, and there is full access to the clubhouse, and better quality food and drinks there, than at other resorts. 

Hey Jon would recommend checking out FB groups if you aren't local (looks like you're based in the Bay).

@Jared Goldwasseri would strongly recommend you go to Cincinnati in person. 

I recommend considering your cash flow and debt-to-income ratio before making a decision, and consulting with a financial advisor to tailor the choice to your specific needs.Good luck!

@Simon Packman - This year I got insurance for a quadplex through Steadily Insurance (Broker) that I've been happy with, so I would recommend giving them a call.

I know you want to go full time and jump in, but I'd recommend staying with your day job as long as you can - it makes your life a lot more comfortable to have a steady stream of income to pay the bills every month!

Honestly looking at your situation I'm not sure I would recommend you do the taxes yourself,  change of accounting method (F 3115) isn't easy for someone that hadn't done them before these online software companies make things seem easier than what they are, they are good for less complex situations.