Sorry for venting but I wanted to get it out on 'paper'. In the end I think I made the right call but still the "what ifs" and "man it would've been cool ifs" are still lingering.

So, like most newbies, it's been YouTube and podcasts for about the past year. So I've been slowly looking and wanting to take the next step. I strategy is: buy > fix up > hold/rent and eventually replace my W2 (maybe my wife's first idk)

Deets: REO in my neighborhood. Pics look rough, it appears to need a roof but after walking it with a contractor buddy, it appears to just be the gutters (some wall interior wall damage but drywall is cheap). But it's rough, we figured it probably needs 80-90k in repairs. Bank has it listed for 164,9. Say 265k all told. Those size houses are doing for 300 around here.

Problems:

1. I don't have crews that could do the work quickly. My 'advisor' friend does so I asked him to look at it through my glasses. I have a W2 so this would be a side thing plus IF I could find guys to do the work.
2. Financing. I really don't understand it. I've bought 2 houses but it was FHA both times. First time buyer > sold > rolled that into new house for wife and I. Called buddy's lender and it was 2 loans, one for the house and one for the redo. 8.5% First 6 months interest only then converts to 15yr fixed. I'm thinking I could swing the note during the reno but if anything happens, emergency, laid off from my job, it'd send me into a tailspin. I could technically swing it but it'd really be close to the line.
3. What if I couldn't rent/sell it. Vague I know but it's something to think about.

So it was a 'last minute' thing. Realtor said the bank was taking bids and will decide on the 5th. I'd only walked the house once and spoke to the lender once. It seemed super rushed and I had a ton of questions without answers, so I passed. I felt shitty, kinda Chicken Little tbh but at the same time, felt like it was the right thing to do. I had too many unanswered questions...

Well the 5th came and went and the house is still for sale. Buddy texted and said they probably had a bunch of low ball offers and asked if I was still interested. I passed again and he said he was gonna go take another look and didn't want to step on my toes. I told him I figured it was better for someone like him anyways that has crews that can jump right in and get to work.

Still feels bad man. It 'feels' like I let a deal get away but I really don't have data to prove it. Maybe I'm wrong but I don't think I should trust my gut on RE investing... I do have a soft spot for the property though, it's literally 2 blocks away.

Anyways, I think I need to learn about financing so if the next one pops up, I'm ready.