We like the short-term rental idea because we could stay at the property ourselves when we want - summer break, spring/winter breaks, etc.Our budget will be right around $1M or less ideally, and we would like a short distance to the ocean.How likely is it that we could find a property as described above and have it cover or come close to covering the mortgage? 

It will likely be a “commuter” community and will still attract plenty of great tenants.

With regard to the proximity to the beach, I tend to have a beach distance of 15 min or 5 mile rule, whichever is less. 

This is a beautiful house - rehabbed/looking new and fresh - walking distance to the water etc, yet low gross yield  compared to Byrd (???)

In terms of distance I will be about half hour away so not bad at all.

I have seen two cases where it went the distance and the buyers successfully sued for specific performance.

I have a list of them that I can share with you.Chicago, without a doubt, has some downsides, but there are also a lot of positives, like the inventory of older multi-family properties and price points at all levels.Investing out-state can be challenging because of the distance and the need for boots on the ground that you can trust 100%.

@Phil SheltonYou would need a civil engineer to provide a drawing to get submitted to zoning and get a permit if it passes zoning is most common This also depends on the road - if it’s a state road forget it as it will take a year to get approved and cost a fortune - if it’s a local road process not as cumbersome but don’t expect this to happen quicklyIn some instances you may have to prepare sight distances etc to make sure it’s safe to add a curb cut

SetbacksSetbacks are the minimum distance the ADU must be from the property lines and it all comes down to the specific zoning you are in.

I used a PM in the DR because it was just easier, especially with the language barrier and definite distance issues but I did co-host the listing on Airbnb.