One final tip is to store the Notebook files on your OneDrive and make them accessible and synced across devices while still keeping them private.

I did all the repairs per spec and under budget and was even able to add four palm trees to the front, a pool heater and fence in the backyard which should have made the value go up! 

Anyone have tips on the best all in one self management software?

Amenities include a pool, spa, big covered deck, fishing pond, hiking trails.

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Thanks for the tip!

But if you were planning to house hack for a long time there then I’d think it would be a better option then renting.Things id be aware of house hacking anywhere near Boston:-Make sure you pick a town with a decent renting pool-Appreciation will be your best friend, not cash flow-Be prepared to spend on renovations always happy to share my experiences or resources if you want to connect! 

My recommendations may be similar to everyone else, but these are my thoughts.Put the word "pool" in your title, it helps when people search for a house with a pool. 

@Deirdre Lizio thanks for the tips on foreign taxation, however that should not be an issue for us as we are not actually planning to stay in one place but rather be digital nomads.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.