We have a good cleaning team and handyman if needed.It isn't that hard really, but remember, your usage must be 14 days per year or less if you want to take advantage of all the deduction of expenses for running a vacation rental home.As far as loans go, we just applied for a 2nd home loan and that was that.

If the laws weren't so tight, this could be ideal where everyone has a way out of a bad situation.

This is an ideal rental property for college students.

However, ideally you'd be finding a great deal that is much lower below market value. 

Ideally we want a cash flow of 3k on next investment, which is hard to find a Boston market.

@Warren Kong I would review with an attorney and ideally use your own documents.

Just remember that certain activities require certain licensure-- e.g. an RIA licensed for some of the activities described above.

Like all buy & hold rental investors it would be ideal to have equity, appreciation, and cashflow off the bat if possible, with responsible and friendly tenants that earn 3X the rent on auto-pay with no maintenance issues!!  

Ideally for every $1 invested in rehab you achieve at least $2 of value. 

Assuming you have your "ideal renter criteria" fine tuned and polished, pre-screening questions can help to weed out unqualified applicants.