I find full replacement cost generally is prohibitively expensive, for instance we bought a property in 2012 that is a rehabbed school that is all brick and will outlive me and my children.

(License numbers are not required in advertisements, but they are not prohibited.)

I informed Bob before entering into any of this that we would need to run a credit and background check on him to ensure he could, in fact, qualify for financing, I would need to inspect the property, and would need to confirm the HOA would not prohibit this transaction in any way.

Is the issue that you cannot prohibit subletting in NY?

There's a federal moratorium on evictions on any property with a Freddie or Fannie loan in place, among other fed programs.It is a conventional loan, but I believe the CARES Act only prohibits eviction for nonpayment of rent.

So the tenant wIllfully illegally brings a cat in knowing darn well it’s prohibited in the lease then when given a stern written warning in a quit notice they still refuse and are justifying themselves ... it’s time to file for eviction .

I also wanted to get my license to gain access to the MLS and be able to participate in certain transactions that I would normally not be able to as an unlicensed investor.My question is: Is there anyone else in this type of situation where you are working with a company that prohibits certain real estate transaction activity? 

I know of at least one structure to do this which passes IRS muster, but it is likely to be prohibitively expensive:Form the LLC Draw up a promissory note from the llc to the IRAStructure the note as a convertible bond with a fixed interest (which can be adjusted by mutual consent)Note converts to equity upon sale (equity kicker)Hurdles: I believe this is bank dependent but common...IRA will have to own less than 20% of the equity so as not to be on the note, so the IRAs interest received should work out to about 50% of the return minus the 20% in an equal partnershipUBIT will need to be paid in the financed portion (not awful)Bank needs to be informed and agree to the bond being in second positionYou will likely need an IRA custodian sign offDon't try this at home!

I guess it comes down to how much time I'm personally willing and able to invest while having a family and full time job and if the stretching of the time from purchase to re-sale would be cost prohibitive or not... just so much to learn.  

In normal circumstances, you are prohibited from having 2 FHA loans entirely unless either your family unit grew (meaning, you need a larger home) or your job transferred you changing your commute time (generally 90 miles difference is needed).