People not doing them is annoying.

After that, it will be following up with them.In sales, people work with folks they like and/or trust.

By being "disregarded," it does NOT mean that the entity has no legal standing --- some people think the limited liability protection is reduced or not there because of this tax filing status.Hope this helps. 

Although, this does not solve your problem, you are not alone.

It's important to know that some software is made for property managers (those who manage other people's properties,) some are made for landlords (those who manage their own properties,) some are made for accounting (which can be used by both property managers and landlords.)I do use QuickBooks, and I'm NOT saying not to use it, but know that there is some initial learning curve that you have to go through.

I am one of these “soft” people that Nathan refers to.

I know there does not seem to be a strong presence on BP for people in the New River Valley area (Pulaski, Radford, Blacksburg, Roanoke) but I would like to try and get some type of networking event going (either in person or in an online group). 

Would love to get seasoned investors' advice on how they would solve this investment/tax challenge: I am about to transfer 300k from a retirement vehicle so that I can use the money to retire early.

Who you vote for has consequences.Unfortunately, a lot of people are voting for politicians that want to take away private property rights and determine what you can do with your property, how you do it, when you do it, how much you can charge for it, etc.Thanks to the large percentage of illegal short-term rentals, and the poorly run ones, you can expect more and more crackdowns in the coming years.

This entails building personal/working relationships with people successful in the field.