However, this is a totally new space to me- Any advice for how to go about looking for a lawyer who works with individual investors and won't break the bank?

Once the municipal/state requirements are all set, do a thorough screening for any prospective tenants, have a solid lease ready to go, and take move-in pictures to have on record for any security deposit deductions after they move out.

Refinancing both at the same time could save you money in the long run and streamline the process, as you'd only have to go through appraisals and closing costs once.HELOC vs.

I will agree that 4 unit owner occupied is a great way to go if you can manage it.

It will continue to go up until it doesn't.

I am very new to real estate as well and I am in a similar predicament as you in terms of desiring that handholding so that you don't make a costly mistake.

Would it be advisable to move my LLC from Florida to Delaware also in the event I need to go to court to recover the loan would an llc in Delaware be better? 

It would be worth paying a third party to go and check the work for you to confirm it's completed before sending the funds. 

OR Talk with a property management team that specializes in Padsplit / Co-living and they can give you some more realistic numbers to go with when it comes to occurancy % and cost!

To me it wouldn’t be worth the trouble to go after the other person or worth the potential liability of it happening again and possibly hurting someone.