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?

1. probably the easiest and least complex options - also should not be really any more cost than opening a single member entity tbh...ensure that dissolution clauses are properly drafted for you both being on title2. for one rental property, this is overkill (although there are many people that will say you need to do this...the maintenance and cost of a trust for one rental property is likely not profitable) 3. personal name with good insurance policy if you're worried about liabilityHappy to go over ideas.

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.

However, the method of handling the 1099 income on the tax return may vary depending on the circumstances and interpretation of tax laws.The approach your CPA has taken, where each property is reported separately on Schedule E and then adjusted on a statement for property 3 to match the total 1099 income, could be viewed as a cautious approach to ensure compliance with IRS reporting requirements.

Quote from @John Underwood: This could be ugly for people who own STR's in Hawaii.https://www.sfgate.com/hawaii/article/hawaii-short-term-rental-vacation-bill-19382321.php Once we have our own property with maintenance paid by HOA and location is 4 meters from surfing spot and mortgage is paid by airbnb renter , all financial metrics no longer apply lol

I understand the title insurance fee itself may be set by the state.It means that I am familiar with the nuances and requirements of investor-type deals that are not present in "traditional" retail deals.

My partner is experienced in landscaping and maintenance for apartment complexes.