It took a year of painful lessons (the first of which is that NOBODY will care about your business as much as you do (Evolve), and that - in my case at least- self managing makes more sense -even remotely- than allowing someone else who has different motivations to take the reigns. 

Based on my experience, you're right that many lenders allow the use of a second home mortgage for properties intended for personal use, provided you meet certain conditions.

Not aware of a lender that will allow a rookie to do this.Recommend either starting smaller and working your way up to this or partnering with someone you can learn from that can be your lead with lenders, etc.

There are definitely multiple options and some will allow for a set amount of personal transactions per year to waive commission splits.

Given your residency limits, the high prices in NYC and surrounding areas are a challenge, but there are still options in neighborhoods further out within your allowed range, like parts of Queens, Brooklyn, and the Bronx.

@Jake Andronico A reverse 1031 exchange allows you to buy a replacement property before selling your relinquished property, offering flexibility in competitive markets and deferring capital gains taxes.

Yes you can but it depends on the lender some lenders do not allow due to overlays and in house restrictions. 

Some states allow series LLCs as well.

In some very attractive markets like coastal cities I can see it being worth it not to rent the unit or rent it only under very limited circumstances in the low season because the high season is just too lucrative to allow anything to affect those bookings.

Doing this will allow you to see if it's even beneficial to have a brick and mortar storefront.