Here’s a simple approach to finding and working with dependable contractors:Finding ContractorsReferrals: Ask local investors, agents, or property managers (especially in REI Facebook groups or BP forums).HomeAdvisor / Angi / Thumbtack: Good for finding reviewed contractors—still vet thoroughly.Visit Home Depot / Lowe’s early AM: Many active contractors grab supplies there and are open to side gigs.Vetting ThemAsk for photos of recent similar jobsGet at least 2–3 bidsCheck license, insurance, and referencesTimingAfter inspection is better you’ll know what you’re definitely dealing with.

I know it's location dependent, and also dependent on how much LTR and STR rates are. 

It really just depends on what the opening bid is going to be.

That depends on where it's located.

There may be a path forward here depending on the answers here, especially since you have new construction experience. 

Within an hour and under $300K, here are a few areas worth considering:Berwyn and Cicero – solid demand, older homes with value-add potential, and close to the city.Blue Island, Oak Lawn, and Evergreen Park – decent margins and good resale activity.Elgin and parts of Aurora – growing suburbs with affordable entry points and improving comps.Joliet – still investor-friendly, with solid rental and resale markets.Each area has its own pros/cons depending on your exit strategy.

@Stuart Tollison sellers concessions is depending of the type of the loan FHA max is 6%Conventional max 3%Only can be used as closing costs or buy down.

Some say that kind of leverage has dried up, others say it depends on the deal.

@Ethan Fiore depends what you mean by "set up".If you're looking for the most up to date lease language approved by attorneys in the state of WA, I'd suggest looking at RHAWA forms. 

A general contractor is about as good at design and creating construction documents as an architect is at swinging a hammer.You may or may not need a survey (although usually advised regardless); it depends on the lot, topography, and what you're developing.