Evaluating markets is one thing, but what do you look for in the people you meet in these markets if you can only spend a limited amount of time in person?

All that to be said I don’t think either one is the wrong choice assuming your market doesn’t have capacity limits. 

Lot's of associations have restrictions on rentals which would severely limit your earning potential/ability to rent at all.

My understanding of loans and financing is pretty limited.

The Home possible program from Freddie is one of the programs that was restricted in the past due to income limits but the limits are being revised upwards which will allow more people to utilize freddie's HP to finance a 2-4 unit property with 5% down on conventional.The advantage of HP is that it has lower monthly MI, its conventional financing so not as restrictive as FHA (which can also work for 2-4 units with 3.5% down payment), HP does not require you to meet the FHA SS rule (required on 3-4 unit FHA financed properties).I've seen freddie's income limits go up about 10-20% this year for 2021 so that might allow more people who are looking to "house hack," to utilize this program.HP only allows max 2 financed or owned properties total so its a perfect for someone starting out to house hack.

.:)  All the numbers look great, but the loan won't get bought by Fannie Mae or Freddie Mac because they limit the ltv on units so it's a no go for conventional financing.A DSCR loan will go to 75%. 

Not every update will add significant value, and if the area is rough, you will be limited in how much appreciation you can force through rehabbing the home.

Are there any regulations that would prohibit or limit a refinance based on the current lien holder?

However, I have a limiting factor in my way which is not having a job hence not being able to finance any properties.

Once you get a hold of them , time to negotiate...depending if you can get a decent price locked up will determine/limit what you'd be able to do with it.