Every system you try will have flaws, or you may salivate over a feature that appears in other software.Some familiar names are mentioned frequently: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I recommend conducting thorough research on each app online to understand their offerings, pricing, etc.

I seek zoning variances frequently in Philadelphia, but its a lengthy process and don't personally find it a worthwhile pursuit for legalizing a second unit in a building.

Can you bring your portfolio closer to save on frequent flights to maintain better control/save time?

I don't invest in multi-family properties myself but one of the Bigger Pockets frequent contributors on these threads is Brian Burke, who quite literally wrote the book on this, I am buying a copy myself, but please read, i think an ebook available too, I do passive investing only in multi-tenant triple net retail but have spent hundreds of hours doing my own due diligence.

A lifestyle that they can travel frequently and for longer.

We hear about off market stuff fairly frequently.

No pool needed.As a frequent mountains traveler I will not consider a unit with no view and no hot tub.I am not experienced in Charleston, but from what I know these would be extras and probably not essential for renting. 

My assumption is $0 rent those months other than a holiday week like Thanksgiving Christmas and Easter, where the projections are showing thousands per month.As a frequent traveler to the area, I cannot imagine much rent revenue in Jan, Feb, March, April, Nov, Dec. 

I also see this frequently around Tarrant County...like mostly Tarrant and Parker where there is a oil/gas lease in place. 

There will be some giant surprises to many there when you have to start paying engineers for frequent evaluations and making the structural repairs required.