@Craig HewittWithout any intention of demeaning you whatsoever, I would say that if you can't put together a solid spreadsheet weighing the pros and cons of either option you should most definitely stay away from being a lender.

Don't regret it one bit and I have no intentions to finish.  

Don't want to get off track from your intention.

I realize that there are those who advise trying to do the amount allowed under one entity and then moving on to another entity.IMO, totally bogus.The SAFE Act, which is adopted by the Dodd-Frank Act states that "any method devised" that may be adopted to circumvent the intent of the Act will be included as to meeting the requirements."

If I purchase a short term rental, with the intention of maximizing only year 1 tax benefits do I have to have the STR in service for a FULL year from when it is placed in service, or can it be less than a calendar year? 

Part of my intentions are to clean up the properties and run a more respectable operation.

I've purchased about 30 ppties this way and NONE of them have ever had intentional damage, although I once evicted a tenant that did about $1,000 damage intentionally and I saw a neighbor take a chainsaw to about 20 feet of load bearing wall during an ugly divorce.all cash

Your choice to spin it around to appear that your intention was simply to help, is disingenuous.

Also, I have heard its a good idea to be up front with sellers about your intentions.

I intentionally will sit there when there is a pause.