I want feedback on this idea or how others have handled adding value through doing their own work or if I am better off just finding non-contracting work and leaving it to professionals more. 

Not everyone will win, but you can guarantee that 100% of quitters or non-starters won’t win either.

Read a lot to start off start with non- real estate books like rich dad poor dad and the richest man in Babylon so you could understand the principles.

Your IRA must also provide all the funding for the purchase or use non-recourse loans to the IRA, which does have some tax implications.I have done a number of REI with self directed retirement funds, and they have all been passive. 

I've done several buy/sell with owner financing, but never with a non US seller/owner. 

Assume you'll hear that the house is worth it when it isn't, tenants are good, management will handle everything, it will be easy for you, vacancy and non-payment will not be much of an issue, repairs won't cost that much.Some will be honest, some won't. 

Any experts out there with some insights on non-conforming, grandfathered, weird properties...that might not have similar comps, hence making it harder to find a loan, etc?

Simply put, historic registered buildings generally have no more value as an investment than non listed buildings. 

Using the QRP oans get you the second tier financing options, for example, a Roth IRA can buy real estate on leverage, however, will need a non-recourse loan which is often a fraction high-interest rate and lower LTV.

Loan docs are usually a deed, promissory note, deed of trust, lender's instructions to the title company, and attorney letter of non-representation.