My understanding is that the ballpark standard of "unless it would be outrageously tough" (something along those lines) is what applies if you're doing a rehab, seeking new permits, doing structural changes anyways, and things of that nature.For existing pre-ADA structures, my understanding is that the standard is more along the lines of "if it can be easily/cheaply done, you have to do it."

Great hosts will be good neighbors, will contribute to local tourism and will pay their taxes and permit fees* A major area to improve on the proposal is the 1 hour time-limit for resolving complaints.

The time saved on seeing that bigger picture is worth it to me.

You could also get a line of credit for about $150k (you should be able to borrow 75% of the value.)The reason I suggest this is…1) you save $40-$60k in selling costs. 2) you have a lower blended interest rate (2/3rds at 3.25% and 1/3rd at 7 or 8% instead of the whole $500k at 7 or 8%) saving you another $1k/mo in interest. 3) you only pay interest on that $150k when you actually use it, not from day 1  Unless you hate this property, or want to buy something you can’t afford without selling, that would be my plan.

The balance on my bridge loan is $120,000.

Run the numbers on a basket of deals you're looking at.

I'm with Dan on this one. 1.

I'll keep thinking on these questions! 

I’ve been a serial house hacker in the greater Boston area so happy to connect and share some lessons learned.Multifams inventories are quite low depending on your budget and location preferences.  

out of state is more difficult than advertised. do you already own a primary residence?