Jim your also describing one of the huge benefits of being a transactional RE Broker ..

Internal Revenue Code section 707(c) defines a guaranteed payment for capital as payments that are determined "without regard to the income of the partnership". 

So there could be benefits from starting a new lease for that reason.

I’ve never managed roommates or lived with roommates but I know it will benefit me so if  the triplex doesn’t work out I wouldn’t mind having roommates.

What's the benefit of the $149 sub through TurboTenant?

.—(1) Whenever money is deposited or advanced by a tenant on a rental agreement as security for performance of the rental agreement or as advance rent for other than the next immediate rental period, the landlord or the landlord’s agent shall either:(a) Hold the total amount of such money in a separate non-interest-bearing account in a Florida banking institution for the benefit of the tenant or tenants.

What are the limitations and benefits?

Repairing the sidewalk came down to a risk benefit analysis.

Of course to maximize your tax benefit it needs to be sustainable over time. 

I wouldn't suggest you buy a single-family home to live in because the additional cost outweighs the benefits.