That house will end up costing you more than the 150K that he paid for it. he is only 4 years into a 30 year mortgage when he stopped paying, probably owes 140K on the loan, taxes for the past 11 years plus liens on the house because the town probably had to maintain the property. what would the ARV be after you tear down and build a new house ?

If you want to scale bigger and perhaps leave your W2 (assuming you have one), then you may not be able to cash flow enough from of a small portfolio to maintain or increase your lifestyle.

They took great care of the place, re-did the entire kitchen at their expense & maintained it immaculately.

All of the condos on Front Beach do well during season but some HOA's fail at maintaining the grounds in my opinion.

They occasionally joined the condo boards so they could proactively push their visions of maintaining and repairing the buildings.

Generally, you are signing a lease 10 months in advance, so it should be pretty easy to maintain 100% vacancy.

When well-maintained, they have a ton of charm and historic character that are very desirable.

Are you going to inspect, enforce rules, and maintain your properties or let them gradually disintegrate into slums? 

So if you won't be onsite to maintain, there are several local companies that will manage them for you.

I'm leaning towards condos being easier to maintain vs single family homes.