But it’s clear you’re a smart investor who knows the long-term benefits real estate can bring.I keep reminding myself why I stick with real estate: you can make money every month in four different ways:Cash Flow – Passive income to live on.Appreciation – Long-term property value growth.Depreciation – Tax benefits that reduce your taxable income.Tenants Paying Down the Mortgage – Even if you’re paid off now, this is one of the biggest wealth-building tools for leveraged properties.It sounds like your main struggle is the stress of active management—and trust me, you’re not alone.

I don't care who someone is or who they think they are, it's in the times of the biggest despair it'll show there true character.It is a failed investment if it doesn't work out.

I think that the biggest take-away for me in the project is to avoid crawl spaces - I am claustrophobic and hate to enter crawl spaces anymore. 

One of the biggest benefits we can offer over a hotel or large apt buildings. 

Here are the biggest mistaken assumption unsophisticated investors make when contemplating an investment in a deal1- that the Sponsor is an expert in the field of investment2- that investments, economic markets, financial markets are predictable with any accuracy3- that PROJECTED returns are PROMISED / GUARANTEED returns4- that because they NEED their investment to be liquid the sponsor will provide said liquidity5- that the “deal” is more important than the sponsor. 

I agree with @John Underwood that insurance is the biggest hurdle.

The main property will be my primary residence.My biggest question is, what kind of foundation would you use, (that is to code and will pass inspection/permits in Charlottesville) that is either relatively easy DIY or cheap to outsource.

That was my biggest mistake.

Depending on where it is, your biggest concern should be will the new furnace, AC and hot water tank will still be there after you close.

If you are borrowing for renovations, you will likely have a draw fee in the $100-300 range per draw.Selling costs: biggest one is commissions.