After reading BP books, I see that my father was not actually investing, but rather working a second job.He went from running 25+ rentals to now 2 (sold them to pay for mine and my siblings education) and I have indicated to him I'm interested in getting into the business.

(if relatively recent, more regulation could follow; if it's been in place for many years, that indicates some stability)  How long have people been vacationing in the area (is it recently popular, or has it been popular for decades?)  

COMMISSIONER: Frequent and substantial sales of real property more likely indicate sales in the ordinary course of business, whereas infrequent sales for significant profits are more indicative of real property held as an investment.Tips to get capital gain treatment on the sale: A) If you have an actual investment property and you are a dealer: Maintain separate bookDocument intent to hold the property as investment property in Minutes or other documentsReport expense as investment expense on tax returnB) Insubstantial Nature of the Real Estate ActivityThe frequent buying and selling of real estate indicate the taxpayer is engaged in the trade or business of real estate sales.

Home prices continue to increase at an incredibly fast pace across the country, according to two separate indices released Tuesday, adding to the financial pressures home buyers face amid rising mortgage rates.

Also, take into consideration how well maintained the condo association is as this should be an indication of the financial stability of the association.

The $1M spend by the tenant may indicate plans to stay or cash out on RE to balance books.

I wouldn't use that as an indicator. 

If you're hesitant to do that, it may be an indication that it's a bad idea. 

@Sarah Bower  The questions you're asking indicate that using a Realtor would be in your best interest.MLS is one of the most effective marketing tools there is for residential real estate, but there's a lot more to it than that.Knowing how to price the property. 

The written proposal must indicate Work Items that require permitsand state that repairs are non-structural.