IMO a bigger red flag would be poor record keeping on expenses and other documentation that would indicate property condition.Anyway, you're ultimately purchasing the income stream that *you* can achieve, not what the seller achieved.

@Dan DeGroff - I think you can probably do this as a primary residence since the scenario makes sense (e.g. you travel to Aspen for work during ski season), however, there are some major red flags here that you will need to explain and support during underwriting (e.g.

Another option can be using a Hard Money Lender, a lot of times there is just less red tape involved.

What red flags should I be aware of?

But, the situation you spelled out raises a lot of red flags. 

Large up front deposits are usually a red flag that the contractor doesn’t have operating capital which often  leads to project slow downs.  

That would be a red flag for me personally.

That's a red flag that your new PM doesn't know what they are doing.

If I were going to do anything, I would have shut down the entire thread.You had so many red dots your profile looked like a Lite Brite 😂😂 sorry, mod humor.

All was smooth until the last one, which had red flags I continued to run through.