Would the aim be to at least brake even when it comes to renting it out?

As for HOAs, that's what I was aiming initially both locally as well as near ski resorts (beach resorts are way too far lol)... the few association fees that were disclosed in the MLS's were half or as much as a reasonable monthly rent would be.

We also have a wood stove for supplemental heat in the winter.This past winter we had very little snow.  

Then figure out what occupancy rate you are aiming for and divide your total cost and profit number by the number of days you want to be booked.

Over time it has built up a pretty nice reserve account to help supplement capex and other maintenance repairs.

Pick an end date and take aim.

I would add that profit folk may want to look at % profit to aim for not a dollar amount..  50k on a 1 mil flip is no good :)  much of the active flipping areas in west markets and higher priced markets your talking 500 to 1 mil  in PP and rehab etc..

I am aiming for my sweet spot purchase price around $250-325k hopefully with less than $120k rehab.

The project I had aimed it for was an 16 unit apartment building that we are going to do a full rehab on.

I'd be interested in talking to you about the Multi-Family you have completed, as that is the focus I am aiming for on a second purchase.