While creative financing options are interesting, having more cash on hand seems like it would put me in a much stronger position and open up better opportunities.That said, I’m still curious—at what point do you think someone is truly ‘ready’ to start investing in real estate?

Tenant Default: 0-5% probability of eviction or early lease termination.Section 8: Class A rents are too high and won’t be approved.Vacancies: 5-10%, depending on market conditions.Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Class B Properties:Tenant Pool: Majority of FICO scores 620-680, some blemishes, no convictions/evictions in last 5 years.Tenant Default: 5-10% probability of eviction or early lease termination.Vacancies: 10-15%, depending on market conditions.Cashflow vs Appreciation: Typically, 1-3 years for positive cashflow, balanced amounts of relative rent & value appreciation.Section 8: Class B rents are usually too high for the Section 8 program.Class C Properties:Tenant Pool: Majority of FICO scores 560-620, many blemishes, but should have no convictions/evictions in last 3 years.

Most will cover up to 100% of the renovation costs and 70-90% of the purchase price, depending on factors like the type of property itself, your experience, credit position, and the lender’s specific guidelines.  

@Roger KimBe careful about gifting twice as well - if you own 50% of the home and give him the full 100% of the proceeds, perhaps it could be considered as a gift from you to him of your 50% of the equity (likely recorded by formal deed prior to the sale). 

@Robert StephensonYou’re in a great position!

If I decide to do the repairs and continue renting it, I will cash flow positive a bit, but to get to that point I would have to spend thousands (replace entire electric system, roof replacement, etc). 

One has no mortgage, their other has a HELOC for around $20k remaining and is coming to its 10year term that was established before placing with LLC.My predicament is how/best way to pull equity out of either property for a down payment for the 3 family that is valued around $450k.

@Aristotle KumpisPossible yes likely no unless you have a ton of equity in other deals that can be cross collateralized

I personally think you can successfully market both your property management (PM) and buy/sell real estate services under one brand if you position them correctly.

You could tap the $400k of equity in your primary, but that's a slippery slope with the little financial discipline you appear to have and could quickly lead to bankruptcy.