I try to take the dreamy-picturesque vacation-location out of my mind (or out of the equation) and stick to the numbers, as @Mike Lambert pointed out, it's best to get the facts and data first.

Then print off that list and start calling, fill in your sheet and let the data point you where to go.

I met a realtor off BP out of GB who I would 10/10 recommend - if you'd like his info let me know and I'd be happy to share that with you. 

does propstream not have the data?

(obviously line 28 is based of line 27 data). 

The more recent the data the better and older comps with purchased on low rates are being tossed out.If this is your only property and you're able to keep it as a cash-flowing rental you might consider getting another low-down, owner-occupied conventional loan for a house hack or just another primary.

Just sounds like planning for a lot of cash transfers to me.You don't report them separately on your taxes, and there's plenty of budgeting/tracking software to keep the per-property data separate.

Websites like AirDNA only show current data.

@Mike PerezMetro Detroit (my rental portfolio is here)Purchase: $80k-$130kRent: $1200-$1500ROI: 10-14%Cash flow: $250-$350/doorAppreciation: Double digit (for past 10 years, will gladly send data)Location: C+, B- (suburbs and certain markets)We have over a dozen Fortune 500 companies just in Metro Detroit with huge Healthcare, Auto, mortgage, Amazon fulfillment, and more jobs.The bad reputation comes from OOS investors wanting $20k D market properties.

Even if roommates are paying you separately, this is not a terrible amount of data entry.