The only possible workaround is likely super low LTV (like sub 50) or if its a purchase and basically zero things that would be required to not do SRO if they chose to do a vanilla LTR

Other loan programs don't have home ownership requirement.

The county requires a septic inspection every three years.

We also require initial payments to be made in good funds for rent and security deposit, which helps to solve a lot of the asset verification.

The key highlights of this slate of bills includesAdditional Excise Tax on STRCreation of a statewide STR registryStandardize safety requirements across the stateProtect the ability for local government to zone STR in accordance with their needsThis isn't the first attempt at statewide regulation, and its clear the bills as written would be operationally burdensome to put into place for the state (aka, expensive) and the problems they are trying to solve are not, in all, a result of STR in our communities but of bad tax laws already in existence.

I'm not sure what laws you think are unclear, but the loan requires occupancy within 60 days.

I setup an LLC for my purposes of renting my first home and I am wondering if I need to transfer my mortgage / title of my first home into my LLCs name instead of my wife and my personal names. (1) Is it required for me to transfer the ownership of my first home to my new LLC?

This pair of products would require two separate systems.

You will be required to pay about $400 per month HOA, this gives you and your guests (who are staying with you) access to the 4 pools. 

Here is a link to the Comptroller's guide to the non-resident withholding, which may have answers to your questions: https://www.marylandtaxes.gov/forms/current_forms/withholdin...If link doesn't work the document is called "MARYLAND'S WITHHOLDING REQUIREMENTS for Sales or Transfers of Real Property and Associated Personal Property by Nonresidents" which you should be able to Google.Good luck.