A good starting point is to ask your agent about flood zones, insurance costs, age of roof/HVAC/plumbing, and whether the home has hurricane protection (impact windows, shutters, etc.).

When you have career changes, go from no kids to 3, 4, 5 kids, have an aging parent who needs your attention.... 

Deductions can never offset the 10% early withdrawal penalty on distributions before age 59 and a half.

Upstairs unit makes it tougher, won't get the elderly/aged, and being 3br it will attract the wrong kind but that's where I'd say efforts are best placed, screening for the right sec8 tenant vs a hipster young couple/group. 

Myles,a DSCR loan could alleviate a lot of your burdens (no income verification) if you are maxed on dti or have a unique income situation.

Hunter gatherer, farmer, horse, iron age, steam engine, auto, computer, etc. 

You may already know him as you guys were in the league about the same time (and I believe you're the same age).

I think the rehab size/age of property will dictate things too.

Do you know if they have a requirement for sourced and seasoned fund verification?

Love the energy — 18 is a perfect age to start building real-world investing skills, and bird dogging is a great way to get hands-on experience without a huge upfront risk.One thing I’ve seen work really well for beginners is connecting with local wholesalers and active investors in your area.