We could probably push it to 70k income, but we take all of the good holidays for ourselves, and we have occupancy restrictions to lessen wear and tear on the property.

If anything that might restrict building but I don't see them running out of water for existing homes so wouldn't that mean home values going up because supply would be restricted.What kind of climate risk could occur there?

I don't have any restrictions on pets with the exception of 2 things: no dogs under the age of 1, and breeds listed on my insurance policy that are not accepted. 

Yes, Chicago has strict regulations for short-term rentals, including mandatory registration and zoning restrictions.

That way you can tap into your down payment and whatever equity you built to continue onto the next one.If you're going for a 2 family for 600K with 10% down in lets say jersey city heights and not doing much reno, you're most likely breaking even when you move out of your house hack and rent it fully. 

Downside is that there are many restrictions and laws to navigate. 

I'm wondering if the same lenders who financing STR's would consider Padspits.You may want to check this, but I would imagine that renting via Padsplit would be considered as a STR which have been highly restricted in the city of New Orleans, and the only way you can get a permit recently is to also live in the property.

The worst thing is that states and municipalities are using wildly inflated data that AirDNA and their ilk are pitching to create more and more restrictive zoning laws based on the perception of windfall host profits, further creating challenges to supporting our mortgages in a region with an already long 4-6 month shoulder season.

Many hoa's have restrictions / limits to non-owner occupants allowed in a community / building.

Best practice is to operate as an MTR and backfill with STR guests because if you open up your calendar to STR guests without tight restrictions, you're an STR.