We are managing a duplex at the moment so we don't need a very complex system, but something to help with the accounting would be awesome!

Most of the house we have used technology to automate our processes which allows us to out source our entire system.

While the wealth of knowledge and experience on BiggerPockets is wide and deep, I would not trust a decision like this to the internet, I would ask you CPA and if you do not have one find one who specializes in this sort of thing.

What's your strategy when you run into guests who are trying to game the system? 

Get yourself a fancy CRM system to handle all that precious investor data.

I do this work for large commercial building fire alarm and sprinkler system submittals.

Every system you try will have flaws or you'll salivate over a feature that shows up in other software.

STR's aren't impossible here, but depending on the area, you'll find them to be extremely seasonal.Other strategies that have worked for me and my clients is the MTR route, there's a robust hospital system in both NYC & LI that is always hiring contracted nurses for 3-6 months contracts. 

Hi Ricardo, my best advice is to work with someone who is also an investor and can easily plug you in with their systems and network of GCs, lenders, and PMs.

It is a very system-driven profession and shouldn't be jumped into without the intention of building a business around it.