• Any structures you didn’t initially consider but ended up working well?

The 27.5-year structural components do not.For example, if a study reclassifies ~$150K combined across both properties into short-life assets, a large portion could be deducted immediately under the bonus rules tied to those original service years, with the remainder depreciated over 5, 7, or 15 years instead of 27.5.

Not a big deal, but just assume an extra 20k of work you’ll need to shell out when you’re buying old homes without PVC clean outs.

You’re in the spot a lot of owners hit — it’s not a “good vs bad” choice, it’s a risk vs certainty decision.Right now the numbers are telling you something important: as a rental, this property is structurally negative by about $1,200/month.

In MA, it helps to be a little more structured than that.Here’s what I recommend focusing on:Income verification + pay stubs/bank statements (document everything)Rental history (prior landlord references + payment history)Debt-to-income / affordability (helps avoid issues mid-lease)Consistency across the application (missing info, mismatched dates, etc.)Biggest mistake I see: rushing screening to avoid vacancy… then paying for it later with nonpayment, damage, or constant drama.Always use consistent screening criteria for every applicant and follow Fair Housing guidelines.

Personally, I use a structured log system that timestamps entries and keeps everything organized in case it’s ever questioned, which gives me peace of mind without overthinking it.

Single-family and commercial investing are very different: single-family homes are usually more approachable and influenced by comparable sales, while commercial deals are driven more by income and deal structure. 

As a fellow attorney, I am sure you are already risk-averse.You’re in a great position to start strong with a solid legal structure.

I do have a couple of practical questions, if you don’t mind sharing your approach: How do you typically structure the option fee?

I would guide you here that your ARV is your responsibility but if your HML is not inline with your estimations, then it's an issue.In the 3rd paragraph, this also sounds like a common BRRRR structure as well.