For short-term rentals (STR), the IRS requires you to prorate NORMAL depreciation based on the time the property is available for rent, not when you purchased it.

Maybe every city is like that, but for me more than almost any other city I have been too I think you really have to know the area and have to know the tenant base. 

It's an extremely clear lease clause, tenant gets discount based on painting of rooms landlord chooses.

With the idea of "we can turn money today into more money tomorrow by investing it," I place most of this within a taxable brokerage account where it grows based on the market broadly speaking.

I have a separate account for my real estate properties and keep a base amount there.

So creating all these funky financials is great, but if you are using those in a presentation that information should be in the PPM or an official document as if someone is making a decision based on that - it can come back to bite them.

Obviously you said you are very experienced so I'm sure thats based on that. 

Key Steps Before ProceedingContact the Loan Servicer: They will guide you through the assumption process and confirm whether an entity can participate.Consult an Attorney: If you’re considering title transfers or joint ventures, an attorney familiar with VA loans can help you navigate potential risks.Understand Due-On-Sale Clauses: Ensure any post-assumption changes comply with the loan terms to avoid triggering repayment demands.Final ThoughtsVA loans are a unique and valuable financing tool, but the program’s focus on personal borrowers makes entity-based assumptions unlikely.

This is public info and usually it will change based on seller being there a long time or something like an elderly tax rate.What are insurance costs like (we've got a lot of local variability around fire insurance for ex.)?

They will likely count your potential rent as part of their analysis and should give you a good idea of how much you could "buy" based on your situation.