In reality our properties in better locations have provided much better overall returns, with so much less difficulty.

That’s not the greatest business model.Trust me, I understand the difficulties of the construction industry.

"My ROI is 80%"... and then you come to find out that it's true but... that is really only $100/mo. or less in actual cash-flow OR they tout high cash-flow but fail to tell you all the economic vacancy they experience, the difficulty with local government and the difficulty in dealing with the lower grade of tenant. 

I've read a lot if posts about the difficulty of vacating a tenant, how would one go about raising the rent for said tenant?

No limitations on that except for the difficulty with financing as I mentioned above.You did hit on the key point I'm wrestling with.

I found one after some difficulties and we’ve spent about 20 hours getting my last years books done and this years books done to date.

@Michael AndersonIf your realtor is telling you that it's extremely difficult, I would assume that your expectation is too high for that market and they are trying to be kind.

As we haven’t established one yet, can anyone comment on the difficulty in transferring a property from individual ownership into an LLC, or should we establish the LLC first and have the LLC “purchase” the property directly from the seller?

Yes, tenant management software will save you time in the long run and allow you to scale without difficulty.

You'll have some difficulties qualifying for a Loan.