Holding it for investment purposes in an S-Corp is what triggers what I mentioned before.If you're flipping in an S-Corp and you have a property that you want to then keep, it's best to transfer it off to another entity in some manner, whether that's a sale or a transfer or whatever.

@Linda Weygant has given you great advice in regards to when long-term capital gains are triggered.

I got smacked on a property when my purchase triggered an assessment which meant the taxes shot up 30%!!!  

Any of those things would trigger a no and you move on to a "qualified" tenant. 2.

But until then am soaking up everything I can for the right time to pull the trigger. 

We can keep their current insurance company or go with our own, but that we would need to keep the insurance in their name to not trigger any due on sale clause.  

But if you do not build out further than your existing porch, that should not be a problem, but you should give them a revised drawing. even a second floor addition that follows the existing structure may need to go before zoning because the set backs may have changed since the house was built and would trigger a variance. it doesn't hurt to ask them and ask what they would require, it would show them that you aren't trying to put anything past them.

Hi Tory,If you will be lending and securing the loan out of state, the law of the state where you are securing the loan would most likely apply, but I'm sure there are exceptions to this.I would think that you need to check for the laws in Massachusetts also.In California and in other states, but not all, you must be a licensed to secure loans with real estate, there are probably exceptions to this rule.If you secure loans with real estate in California with a licensed broker, the loan is exempt from usury laws, again, there are exceptions to this rule like lending less than 30k in senior position (or less than 20k in junior position) and there is something that attorneys talk about regarding charging an unconscionable rate but that would be getting way too detailed...Another important consideration is that if the proceeds of the loan are used for personal use or if the collateral will be owner occupied, then that triggers a bunch of other regulations, this is why most hard money lenders only lender for non owner occupy business purpose.

Additionally, once I have the loan pressure is on to take the first offer I’m given because of the daily interest costs on the loan, I’ve lost out on an extra $30k on one deal because I pulled the trigger 10 days too early on an offer.I’ve tried to present bankers an offer to fund the loan but I haven’t found the right “combination” as Brandon Turner likes to call it.  

Fewer pull the trigger.