I have had instances where the weatherization was not done properly and incurred damages, usually from pipe elbows that there not blown out and developed cracks from freezing water.I currently have a house that is rented but the owners are not residing there until after March (complicated story).

Compare large syndication sponsors with tons of experience to a newbie investor and the risk scale shifts hard in favor of experience.I'm sure there's a decent chance that a sponsor encounters a complication and drops a few percentage points on the IRR to their investors.

If you don't; it gets a little bit more complicated as you would need to calculate the wages allocated to each state.

In short, it's way more complicated than you realize, and you're talking about doing it on deals that are impossible to find in the first place.With regards to marketing to distressed sellers - there are entire sections of these forums dedicated to just that. 

So it would be appraised as the value of an empty lot, less the cost to demolish and remove the structure.Things can get complicated though, because sometimes if a structure is demolished, they apply current zoning code to determine if something new can be built there.

It's complicated at first but it will become second nature.

We want to work around this by paying her directly, but I'm worried that the tax picture would become more complicated without a withholding company (which is what I'm assuming Upwork is).

Of course not - don't make this more complicated than it needs to be when you are starting out.

I also like the idea of an extra amount held in escrow but that could get complicated/expensive quick, not to mention opening you up to a future lawsuit if the seller disagrees with how the money is disbursed. 

Further complications.