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*This link comes directly from our calculators, based on information input by the member who posted.I’m considering purchasing two investment condos to help pay for my children’s college tuition in 13 to ...

My experience with S8: There is a reasonably strong correlation between S8 tenants and tenants that do not take care of a rental property. 

Beyond carefully vetting the tenants, how can an investor protect themselves from squatters if we want to sell years down the road?

I like that lawn and snow removal is taken care of in an association, but dislike that expense each month. 

(To avoid months of probate and thousands if not $10’s of thousands of dollars in costs.)Hawaii is considered a "TOD deed state," meaning that residents can utilize Transfer on Death (TOD) deeds to designate beneficiaries who will inherit their property upon their death, allowing for a potential bypass of probate court proceedings.If she is already in memory care center.

No one cares about your properties like you do.

Is this pocket a value oriented area (most sq ft per dollar of rent) or will they care more about proximity to highways, retail, walkability?  

My advice is to tread carefully.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Someone that tweaks the pricing and reviews?