(Smaller investor - holding properties in just one entity)My Must-haves:- manage multi portfolios- document management- auto import/connections to bank accounts- ability to handle tenant payments within the system (there are many varying levels of this across the spectrum, I just need a subset)- end of year/reporting/tax prep help- maintenance request workflow (with tenant and contractor logins/communication)What I really like about stessa - - low cost- the dashboards- unit listing and application/screeningwhat i do not like about stessa- sometimes broken-ness of bank connectivity- they went from free to paid and took away features and didnt grandfather existing users- lack of maintenance trackingI have not tried the application screening process in stessa yet.

and also utilize an umbrella policy to give you extra liability coverage which can extend over not just your rental properties but also your personal properties and auto policies. 

@Darrell TaylorYou could buy 4-5 cash flowing metro detroit rentals and make $1000-$1500+ a month in cash flow and double digit roi.15-20% down + $5-$6k closing costs:Metro Detroit (my rental portfolio is here)Purchase: $80k-$130kRent: $1200-$1450ROI: Double DigitCash flow: couple hundred/monthAppreciation: 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 and Auto industries.

But I won't surprise to hear someone shout at me again and say "that is HORRIBLE..." because you guys really know how to make the money rolls like a ball.I had my auto insurance with COSTCO - Ameriprise Auto&Home Insurance (1-888-404-5365) since 2006.

It's like an auto insurance.

That's all we said to him about it, as we wanted to weigh the various pros and cons.Next thing I know I get auto-letters from our lender saying they've pulled our credit (the required "this is your credit score" letter), and our agent has sent us an email saying our lender told him that we'd be approved on such-n-such terms, blah blah.I don't appreciate our credit being pulled without our permission, or our lender and agent discussing our finances and approval status together, much less without our knowledge or consent or even saying we were ready to move forward. 

They sound the same, and in auto insurance the terms seem to be used the same, but it is very different in rental property.

I have one agent that can combine personal auto, home, and up to 9 more properties and it passes the combined home/auto discount onto the rental properties but I don't know if he can offer that to out of state investors. 

-  auto bill as much as possible.  

That is not hard to do.A good estate plan will address all RE management issues as it is designed to adminster your estate on auto pilot so to speak, your RE continues to operate without you.