Obviously, the funds and syndication world has its own SEC exemptions, and you can invest all day in Reg A offerings or 506(b) offerings.  

Is there in wiggle room in the 2 in 5 years in order to meet the $500k capital gains exemption? 

John If primary residency you can claim the tax exemption, but need to report rental income and pay taxes for that. 

@Kaycie GunnIf you want debt financing hard money or private money lenders will fund with typically 25% down paymentIf you are looking to syndicate and raise money from investors then that is a different animal and you will need to file an sec exemption to raise money and depending on your experience it could be moderately challenging to near impossible.

I read online that a transfer from Parent to Child is exempt from real estate transfer tax. 

I actually meet several exemptions based on the type of lending I do, but here is one of them...

But $5000 just to determine your tax liability and run scenarios on outcomes of a 1031 exchange and tell you if you qualify for a 121 exemption??? 

Additionally, you may qualify for the owner occupant exemption if you live in a unit within a 4-plex (or smaller), where you would technically be exempt from the fair housing act, but this exemption may not extend to your individual state or municipality. 

@Bruce Lynn  @David Cheng The good news here is the condo projects that are 2-4 units are exempt from the project review that trips up so many condo's for conventional  financing. https://selling-guide.fanniemae.com/sel/b4-2.1-02/waiver-pro...

Homestead Exemptions If this is your primary residence, then apply for the homestead property tax exemption and any other exemptions that you qualify for.