My wife and I recently closed on a STR property in the Baraboo area and want to ensure we are doing everything the legal way. 

Remember that you would not be investing personally but rather your IRA, which is a separate legal entity.

I would argue that the premium is valid due to the value I added to the property by getting the legal structure and agreements in place, then finding like-minded buyers.I'm looking for people to poke holes in my logic.

Is it legal?  

A lot of people try to manage property without a license, but since these folks defeated the first eviction they may have legal assistance.

@Jefferson BlackJust make sure you have the proper COs, and it is in fact a legal Triplex.What is your exit strategy on this deal?

Agents are not legally able to do inspections. 

Transferring ownership to the new LLC is possible but may have tax or legal implications.Let me know if you need further assistance with financing!

State costs vary, but more or less should be +/- $750-1000 to get obtain your NMLS mortgage license (with courses) and most states permit dual licensing in which brokers can be legally compensated on both sides of a transaction.I'd be very cautious about performing dual capacities in any single transaction for two reasons: 1. 

Since the Internal Revenue Service (IRS) doesn’t consider child support taxable income, I would not consider it in the rent calculation unless you have a HUD-specific home.According to hud.gov, “[rental property] owners must count alimony or child support amounts awarded by the court unless the applicant certifies that payments are not being made and that he or she has taken all reasonable legal actions to collect amounts due, including filing with the appropriate courts or agencies responsible for enforcing payment.”So, does child support count as income for renting?