Regardless of whether the owner turns a profit, brokers are called up on to sell, lease and manage, lenders will finance, contractors (often affiliated with PM companies will be called upon to put out the constant fires).

Could you recommend a trustworthy and cost-effective company for this? 

Hi Jon from Boyertown, PA-You and your fiancé are interested in buying your first short-term rental and wonder profitable areas to purchase with a budget up to $500,000.I would look at places along the west coast of Michigan, Grand Rapids, Kalamazoo, and near Ann Arbor, MI.It is important to understand the local STR regulations in each community and partner with a property management company that can help your navigate that and manage it well for an excellent guest experience.Don't forget to look into bonus depreciation and doing a cost segregation study to increase the tax benefits of ownership and if you "materially participate" in the management of the property per IRS guidelines it can offset active W-2 income which most real estate cannot.To Your Success!

It's best to invest in a company/fund that does this for you. 

Looking at this past week's CMI, it's interesting to see the buyer/seller positioning in the SE-ish area compared to the NW-ish area with rates high 6's in JanuaryStill bullish on W/NW future demand due to TSMC factory and other companies (dashboard snapshot below) but time will tell.

Since the previous owner is getting most of the proceeds does the closing attorney issue him a 1099S and then issue my company one for a much lower amount?

You can use the Bigger Pockets management finder tool to look up MTR management companies in the area and then I have a few recs I can provide if you are interested.Shoot me a message if you would like to discuss further and I can help you strategize to make sure you make the best decision possible!

There are specialty umbrella companies that don't require you use them for car and home.2.

Will a title company do that? 

The credit unions in my area only work with bigger companies so just know I have already reached out.