Personally, I would not create a conversation around this "risk" as that is a sure fire way to increase the sellers anxiety. 

Starting your journey into LTRs and flipping is exciting, and creating solid business and marketing plans is crucial for your success.

*This post does not create a CPA-client relationship.

When renovating a walk-out single-family home to create a separate legal unit in the basement, removing the interior stairs can increase usable square footage and enhance security between the two units.

You'll for sure get those costs later.If you're looking for a sub $300k market in the SE, I'd pursue college towns with good athletic programs and create small STRs but be ready for the seasonality.

You can create custom maps to mark areas of interest, track properties you're considering, and note key amenities like schools, shopping centers, and public transport.

You can self-promote under the Classifieds forum.Regarding cash buyers list you are trying to create - just find solid deals and publish them and the buyers will appear.

I’d love to have real estate provide some financial freedom/flexibility and create a portfolio that I could eventually get my kids involved with and pass down to them, but I end up feeling frozen/stuck based on the factors above. 

If you can get a 4 unit and a basement, that would be ideal and create major cash flow and equity creation, plus you can not worry about a property manager and boost your yield.You can get a whole bunch of cheap debt which your tenants will pay down over time, massive appreciation and potential cash flow if you buy right. 

They will likely also need to close any access points to satisfy city inspectors that the now capped chimney cannot be used to "vent" anything in the future.You will likely want a demo team that is much cheaper to do the actual demo and haul off, but you need either the mason or an engineer to stipulate how far down they can/should demo, while leaving enough room for the cap to be effective and maintain any structural rigidity into the future to not create more issues.Long story longer, I would call more licensed, insured contractors.