If you have equity and decent credit, a conventional Fannie Mae HomeStyle (or the Freddie Mac version) would likely be the better option instead of an FHA 203k loan (which will require a 3rd party HUD consultant to oversee the deal in addition to having the contractor involved). 

R.E. agents/brokers now have ALL tools, options, networks readily available. 

Off-market deals give you control over pricing, terms, and creative financing options.

I was looking for some advice (viable target areas in Cleveland or Ohio in general, financing options and credible PM/realtor contacts) from the experts here though especially if you are in a similar boat as mine (reside in Canada/Ontario area and invest in US). 

If you’re still looking for insights or financing options to scale your investments in Jacksonville, I’d be happy to help.

To answer some of your questions, I’ve been in it for 9 years my intention was just to live there but then I got the investing bug so not I’m seeing what options I have.

So a loss of about 55k We did a lease to own option so I could immediately take over expenses but keep their primary resident loan and interest rate.We agreed to a deal which would cover all their expenses at closing, their remaining loan balance, and $45,000.

any suggestions on how I should compare these 2 options?

Florida, particularly Tampa and Central Florida, is a strong option because of steady demand, landlord-friendly laws, and solid appreciation.If you’re debating between short-term and long-term rentals, I’d say long-term rentals are more stable, especially with the recent saturation of Airbnbs.

It'll likely be much lower.Of course - on subsequent years the property tax footprint can rise by no more than 5% YoY.I'm trying to dial in my P&L here, so if I do find a decent investment property option, the math can be done quickly and I can get moving quickly.