I also realize, or have been told, that everything is negotiable so while I would prefer to work for #1 as the owner/managing broker is like family, they are a national company with better lead-generating systems, education, etc., the required monthly fees starting out are intimidating.

Like participation in asset management fees etc. 

I started in Milwaukee after my company has reloacted me here from Austria and I was looking for an alternative to Wallstreet and 401k - so it was not my choice and at the time (fresh of the boat) I would have preferred a more exciting city like NY or LA.

I'd want to check your math (because ROI of 14% seems high on student loan payoff), but I'd take 14% guaranteed ROI all day long.I think we'll see other opinions, though, as there is a 'personal preference' element to the question of reducing debt VS investing.Best of Luck with Your Real Estate Investing!

I have that in my portfolio and in other assets, however I would like to fund it with a loan.

In fact one of our preferred factories has shipped to HI. 

Or should we merely roll all the assets under our current LLC structure (note: our state doesn't care about DBA- you can have 30 companies with the same DBA so long as there are no complaints/TM infringements).Many thanks in advance- and to answer a few questions; no I won't share the name and would appreciate it if others wouldn't as well. 

For federal income tax reporting this means the SMLLC is dissolved and there's no distinction between the SMLLC's assets/income and the owner's assets/income.The tax treatment of you holding the property directly vs through a SMLLC taxed as a disregarded entity will be 100% the same. 

You can do it both ways, but I prefer to just make monthly payments.

You will survive. good underwriter looking at your tax returns will see you own the debt and the asset.. probably gets bounced.. this is what HML did pre 08 all of our loans went to buy and hold folks and we did rate and term refi.. but we were a true third party lender .. its was a great gig while it lasted my average turn on my loans was 92 days.. and the buyers not only had no money in the deal they got refi proceeds usually 5 to 8k a house and they would do 4 and a time.. now they were suppose to take the refi proceeds and put them in their reserve account.. but alas the reserve account ended up having Jets skis in them instead maybe a new car.. or that trip they wanted to take.. etc etc.. anything but where it was suppose to go..