You also want to see a reserve study and only invest in a property where the HOA is at least 30% funded, less than that is assessment territory. 

It's like full dividend re-invest on an index fund.

Assuming that all goes well and the buyer’s good-faith offer is accepted by the seller, the earnest money funds go toward the down payment and closing costs.

Why not joint venture with someone who has money, fix & flip itWhy not rent it out for at least the monthly carrying costs.Why not sell it on a lease option, get 10% cash up front to fund school? 

If you have excellent credit and enough for a down payment/closing costs without totally wiping out your funds, I say go for it!

That said there are some nuances and requirements to property implement interest tracing so ensure you talk to your tax professional ahead of time and keep the funds movement as clean as possible. 

I'm just beginning but am considering a bigger commitment in the next five years or so by accessing some or even all retirement funds to buy a building (I'm sure people have thoughts on whether or not that is a good idea!).

Unless you're in a Class A Neighborhood like Palmer Woods, Indian Village, Sherwood, etc,. the additional rent probably won't support the cost to build:(More profitable to take the build funds and buy another property.DM us if you'd like to discuss more...

I don't know your area, so I can only write to my experiences in PA.You don't really convert your property to Section 8 (S8), but rather sign a lease with a tenant who happens to be funded by S8.

I would acquire in cash and then refi into longer funding. #4.