@Jae Jun: Although the conversation has changed much, and toned down regarding proposed restrictions, the plan from jump has been to allow anyone with an existing STR, so far defined as a place that's been rented STR at least 2 consecutive days in the last 6 months, to get a permit and be grandfathered.

When you start, the company may give you a small existing portfolio, but then you'll have to maintain & grow it to make a decent living.You could also work as a leasing agent at an apartment complex.

I'll subto his existing mortgage and pay off the 120k.

In that case, would the renting process be a bridge to help you retain the home for future personal use? 

Insurance right now is wild, so I'd get a solid broker on your team - I'd be happy to share my contact if that would help.Also, aren't most of the existing insurances shared on the OMs for the properties? 

Unlike refinancing, which involves taking out a new loan, recasting keeps your existing loan terms—including your interest rate and loan duration—intact.

A 50% LTV on a $120K house at 7%, 30 year Am results in a $400/mo interest payment.The cashflow on your existing duplex goes to $1,000 per month, but now you can buy another just like it so yoru cashflow goes to $2,000 per month.  

FlooringScope of Work:Replace carpet in bedrooms with engineered hardwoodRefinish existing hardwood floors in common areasInstall durable tile in wet areas (bathrooms, laundry room)Estimated Cost: $20,0004.

As a first timer with no existing properties and no experience do you recommend looking into long distance investments and managing thing remotely? 

Rates may still be high, but sometimes they’re more flexible with repayment options than a mortgage refi.Family Loan Structure: Since you have an existing interest-free loan from family, you could talk to them about restructuring or even adding onto it, if they’re open to it.