My thoughts were to do a contract for deed and a quit claim deed, but I guess it doesn't make too much sense since I can't file both. 

Afterward, I ask them and if it does not make sense to me, I will not do it.

@David Khalfin If you can get houses in that price range, I don't think it would make sense to build a new home with the money even if you get enough to do so. 

If you took the time out to learn about the hundreds of condos we have in Miami, then working with wholesalers would make greater sense.

Does it make sense to invest about $500/year on a policy for an investment property?

My experience is mainly in multifamily properties as well as commercial investment properties, but I'm not feeling like it makes sense to value this portfolio like I would a single 104 unit property. 

Just make sure you do all your calculations correctly before deciding if this type of move actually will make sense for you.  

In that sense, I'm effectively "borrowing" earning power from my retirement account to make cash flow today. 

@Lauryn Meadows   Congratulations the deal looks good,  I would do one by one, starting with the new ones, numbers need to make sense for you,  but keep in mind that you may get more rent for one unit but how much do you have to invest in order to rent it again.

(Please let me know if this makes sense or not, I’ll try to make it more clear if needed)2.)