You could structure the deal with seller financing to bridge the gap.Possible offer structure:-Purchase Price: $170K - closer to actual value-Down Payment: Low or zero down to conserve cash-Interest Rate: 3%-5% - or better yet, 0% if the seller will agree-Monthly Payments: Interest-only or deferred until the sale-Balloon Payment: Full payoff in two years when you sellIf he wants $200K, you can still make an offer of:-$170K purchase price + $30K as a second lien due at closing-Seller carries $170K at a low interest rateHe would feel closer to his number, but you still keep within reasonable investment limits.2.

• Payment Structure: • What is your payment schedule?

But as far monthly payment you could easily buy a house in a cheaper location have less roommates and the same monthly payment or the same number of roommates and a lower monthly payment.

Many would suggest against RE investing using retirement money but if you go into low risk opportunities it can be a powerful diversification method.

Safeguard strung me along for several months of late partial payments and very little communication.

Whatever I do, I would need to do with a HELOC—effectively financing 100% of the property (down payment and closing financed with HELOC, rest of purchase financed with a mortgage). 

You may be required to make estimated tax payments when the property sells.It depends on what your 2024 total taxes due were and 2025 estimated total taxes / withholding / estimated payments are.If you pay in atleast 90% of the current year tax or 100% / 110%(Depending on 2024 income), you are normally considered good.You may want to consult with an accountant for more clarification.

What methods of investing are you looking to do?

Now I spend 5 years hoping they make their payments and somehow refinance to pay off the balloon. 

100% of the deals I've done with Safeguard have had late payments and/or major issues.