There are a few things you can do and know on the front end to help prepare. 1)Know how to read your loan documents. 2)Know the differences between Cash Trap, Cash Management, and Cash Sweep. 3)Know what a Trigger Event is, and if you have one written into your loan agreement. 4)Know how to efficiently request reserve disbursements.5)Make sure your lender is never holding more than they need to in escrow. 6)Have a system set up to monitor your lender and their obligations, in addition to your own.7)Know how to recognize and monitor risks based on how your loan agreement was written.8)Know when you need to hire an attorney, and when you don’t. 9)Know the difference between Property Management and Asset Management.Already experiencing some of these issues on a Loan?

I know that this can trigger the "due on sale" clause with the lender but I've heard there are ways around this using a land trust? 

I want to pull the trigger anyway since it looks like a good first investment.

(2) I am no aware of a conventional lender who would underwrite an LLC.My suggestion would be to put the existing property into your personal name before the sale, buy the replacement properties under same name, and then consider changing the title to your LLC at a later date - you risk triggering the "due on sale" clause, though.

Hi Billy,Sounds like an ok deal to get your feet wet.As you listed out there are pros and cons to the nicer areas vs lower cost areas to invest...the biggest challenge others face in your shoes is actually pulling the trigger and getting the first deal on the books.

My question is: if we decide to pull the trigger on this deal what are some creative strategies to optimize my return on this land?

HiI pulled the trigger, a couple of months ago, on a 2000 sq ft building in a very busy road frontage location in Ocean Isle Beach, NC.

Those who waited are now in a significantly worse position than they would have been if they pulled the trigger last year and that's only going to get worse if they don't jump in soon.Maybe the market will crash tomorrow morning and they'll be proven right, but I just don't see signs of it happening.  

Be aware that if you have a mortgage on the property, the transfer to an LLC may trigger the due on sale clause (that could be avoided using a land trust).

Under Massachusetts law, it is illegal to discriminate against someone because the presence of children might trigger a property owner's duties under the lead paint laws or because someone receives a housing subsidy, such as a Section 8 voucher, to pay for some or all of their rent.