I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

If you can get over $2500 per month in Jacksonville on a 300K property, good luck, but if you can, that loan is out there. 

I have found that they worked really well when it comes to getting better tenants and better rents, and having less hassle, less headaches, and then getting a higher sales price; without paying closing costs or realtor fees.

I've seen estimates of $200 to $400 per square foot for SoCal with $700 sq ft for something higher end and building up a hill and but possibly higher for San Francisco Bay Area (lhigher labor costs, etc.).  

Profit per door is relevant.

What specific websites will they advertise your vacant property on?

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

I understand I'd take a pay cut being an agent for the first few years, but in exchange, I'd be learning about the market and building a network as I move towards Commercial multifamily.

It would take you a life time of cash flow in Ohio to get that return.I would strongly advise you against paying cash for a $100k property.

Property owners in these areas can only advertise for monthly rentals and are not permitted to offer daily or weekly rentalsandIn March (2024): Florida lawmakers passed legislation granting the state more authority over short-term vacation rentals, potentially impacting local regulations.