We have an entirely too complex PMS for 5 units (Streamline - used on typically 50+ unit portfolios). 

How does your software of choice streamline operations and enhance guest/tenant experiences?

For those of you that have created a strong team (acquisition, contracting, finance, management, etc.) to streamline your investment portfolio--even from out of state--what has worked the best for you and/or what do you wish that you had done differently?

I might think the tenant has poor manners in a situation like that but I wouldn't feel aggrieved in any way since they are just my customer not my friend.

For my multi-family properties, we get quality leads from Apartments.com and Zillow.I believe if you have a bigger pockets pro membership you can get lease agreement customized for any state.

You might have a challenge with tenants/customers feeling uncomfortable next to a prison so getting the local insights might be valuable to you as well. 

Maybe some specialty programs exist for prefab homes or a custom ADU builder might have his own lender partner they could refer you to... but unless you yourself are an experienced home builder with a track record in ground-up construction, you're basically looking at a hard money or a HELOC.

Alternatively, I could go with a custom design; what should be a ballpark price for all architectural and construction related plans?  

I've seen some where the screen does not open while others have the classic squeeze-to-open.I ask because if they do not need to open I can build them myself but otherwise we have weird dimensions and will have to pay $$$ for custom...Thanks in advance!

A super basic step one would be to set up a "newly listed within the last week" custom search on Crexi, Loopnet, whatever.