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? 

Proper underwriting - this includes an appraisal, loan app and full underwriting to comply with CFPB regulations.2.

From what I’ve seen in Forbes, the infromation on market trends can also help pinpoint the best neighborhoods.One last piece I’d consider: do some legwork on rent comparables in the area so you’ll know your break even numbers from day one.

That should really be the deciding factor...is it necessary and a large enough project to include the permit process?

The Homeowners Insurance will include Builder's Risk. 

You want an investment that pays for itself, including mortgage, taxes, insurance, maintenance, and even some money set aside for a reserve to cover vacancies and capital expenditures.

Squatters break into vacant homes, can present fake leases, and are a valid problem, but if you have cameras on the house, you will be able to get them out right away and you will see them going in.

Maintain - includes taxes and insurance?

We cannot grow (land locked) and we have only garbage included in our rent.

We typically pay somewhere in the range of $3500 for a new, basic furnance, including install, if there are no other modifications to the system required.