If you have a realtor he should be helping you get everything you need in the way of inspections and permission to self inspect etc. etc.This deal smells really bad just from the few paragraphs you have written.

or should we open a Self Directed IRA and use that as a vehicle?

You have two choices, hire someone who is willing to teach you how to estimate (online or physical), or self-teach by buying some books like J Scott's book or Construction installation encyclopedia.

Tenants who are reluctant to do this means that they probably don't have sufficient funds in their accounts.

dont overextend your self. there is a right time for everything. if you dont have money, take the time to learn as much as you can. 

I would love to ask the community (experienced or a newbie) a question and feel free to answer below (if you want):What do you wish you could tell past self before you embarked on your investing journey?

Additionally, the reason we hesitate to sell is because we've got an accessory apt in basement with income stream as well as a separate office for where I work every day (self employed).

Conservatively one would assume 8% vacancy (1 month/year) , 10-12% for property management (even if you are self managing, your time isn't free), 4% maintenance and another 4% misc.

That way, the day will come sooner when you can have the entity make the buy rather than buying it your self and having the entity buy it from you to satisfy lender "Due on Sale" issues.You'll want your long term holdings in LLCs and your fix and flips in your S-Corp, C-Corp or whatever.David J Dachtera"Success is not a destination.

If so, just send me a "colleague request" under "connect" and I'll send it.I'm from Canada so I'm not sure what FHA loans are like, but here, if you're self-employed, the bank is more inclined to give you a mortgage if the property makes its own money.