There's a lot of caselaw out there discussing how the federal law on this topic interacts with state law.

So picking a property that requires a lot of interaction is a bad idea.

You should anticipate paying more may be close to 500K for estimating purpose. 

A lot more costs than anticipated, but we had a huge margin for error as well.

I am also very introverted and have been pushing myself way outside my comfort zone the past couple months networking and interacting with investors/property managers/realtors. 

You might find that there are restrictions you can't live with like prohibitions on parking a camper, boat or commercial vehicle - and even the colors you can paint your doors or shutters.Be sure to ask whether there are any pending lawsuits against the condo association or any special assessments in existence now or anticipated in the future.You shou;d also request a certificate of good standing from the condo association, meaning that the seller doesn't have any outstanding fines or fees. 

Keep in mind we do not have known cost amounts for these repair items, and can just make estimates, and hope no other costly issues are uncovered after attacking some of the repairs.My question is, with our next interaction with the selling agent, should we:A) Ask for the major repairs be metB) Ask for a decrease in agreed upon price (without great idea of what the repairs will cost)C) A combination of both; settle with some repairs met, and a decrease in priceOur entire list is below: (keep in mind that I am not sure if all of these things need direct attention to get the unit rent-able, or if some items can be overlooked for now and deal with later as they become more of a problem)Repair List:Items that need attention before renting unit:Big Ticket Items:Install furnaceInstall all new appliancesInstall water heaterExterior electric power supply is damaged, needs repairInstall guttersNo termite treatmentNo gas meter, install newAttic decking has moisture damage, needs repairSmaller Repair Items:Install electric panel faceplate and secure exposed wiresTwo prong outlets (could not test), swap out, install GFCI where neededTrim tree limbs in contact with power linesMissing light cover under front entranceRepair kitchen windowsRepair kitchen sink leakRepair utility room leakInsulate atticSeal gaps in living room doorLoose bathroom faucetAdjust shower water pressurePatchwork performed in multiple rooms, walls are plaster on wood lathe- which I have been told can have asbestos issues once opened upDeferred Cost Items:Large tree removalTorn and missing roof shinglesSeal plumbing boots on roofRaised soffit under car portSecure electrical lines in attic, they run over attic stringers, not through them (necessary?)

Assuming he plans to flip the property after a 6 month rehab I anticipate he will make approx $50,000 - 75,000+ after selling/closing fees.  

If you anticipate making more than 40k per year in profit, you might want to designate S-corp tax status for your LLC.

It is time consuming, but I base the interaction off how much detail they put into their listings.