Additionally, it raises red flags in underwriting if you were to originally acquire a single family home, and then move into multi-family after that.  

Embarrassing, because my seller did exactly that, without any of my loan details, and generated the exact same letter I had given to him.Lessons learned: gold cross = red flag, "have a blessed day" = "see ya"Date of experience: June 16, 2023

If this passes and someone ran their numbers based on 30 day stays, they could see a significant hit to their bottom line.In summary, talk to people who know, ask them what they think will happen in that specific area, and know that in high demand areas an absence of rules can honestly be a red flag - it means the STR conversation hasn't happened yet and leaves you vulnerable to whatever the decision is once it does.

Naturally, at least for me, it raises a yellow flag that they increased it this late into the offering. 

This would be our first rental and I think it could be a good opportunity long-term, but it feels like there’s some red flags here.

@V.G Jason Your characterization of me is odd, in that it’s entirely wrong.

Anyone bragging about how much in assets he has bought with other people's money, while getting non-recourse loans is a huge red flag that it is all hype and ego. 

If you feel these red flags are irreparable, ask for concessions or tell them to peace.

- Are there any red flags or cautionary aspects I should be aware of?

Based on the info you provided, there are strong red flags.