I'm starting out and am debating between Xero or Freshbooks.

I have debated wholesaling just to build capital so I can purchase more buy and hold properties.

If you don't, I doubt that you will end up in trouble, but you might not be in compliance.If someone has a definitive answer about PayPal and Venmo - please chime in.Your second question, about Schedule E landlords and 1099s, has been debated on this forum countless times.

Debating whether I go with an FHA on a duplex, triplex, etc. locally, or just go for conventional 20-25% loan on a single 2 bed apartment in good location.

If it makes you so emotional, best to just avoid the topic and this postYou're the one that can't debate the point with facts & logic. 

I debated for a while but ultimately decided to pull the trigger because I think you gain versatility and additional connections. 

I've been debating this for so long and I just can't decide what's best.

While my monthly cashflow from my employer is more than enough to cover this, I can't scale up like that.The factor that breaks this appreciation-vs-cashflow debate is ask this: Why does it have to be one or the other?

I'm currently debating between trying to find a LTR here locally in NJ or finding a STR that i can manage remotely in a hotspot like Myrtle Beach.

I am debating should I go to college to get a degree in accounting then start working to gain experience but it’s going to slowing me down on my saving process and less time to maximize my income or should I just get a Pre-licensing training instead ?