I worked for 3 years in Boston as a rental agent and have seen way too many unique problems with older homes.

So maybe if you setup a separate company to manage the property, and that company were to have an extremely unique name that when googled led right to your website, that could be a totally legal approach.Why don't you use the listing sites for what they are meant for, then try to market direct to those customers that have already stayed with you without incident for their repeat business?

You have a unique plan which I wrote down and plan to do.

I understand the difference between passive investor, active investor, and real estate professional in the eyes of the IRS, but does investing using an LLC give unique tax advantages too?

$3,200 Costs Gross Income CAP RATE 10.73% 9% YES Mortgage, taxes, insurance and utilities $2,040.44 $38,400.00 CACROI 7.97% 10% NO maintenance and capex $ 640.00 20.0% break even point in months 75 60 NO vacancy $ 320.00 10% NOI $ 199.56 $500 NO down payment $ 12,525.00 5% Tax liability $ (6,714.40) $ - YES Fees $ 2,505.00 1.0% Annual Net Income $ 4,073.29 Cost of Capital Improvements $ 15,000.00 Monthly Profit $ 199.56 1793 TAX Money REVERSE VALUE 21516 Net Income $ 32,627.19 $362,524.30 172128 Depreciation Expense $ 9,109.09 Projected Taxable Income $ (6,714.40) Item Cost Tax rate 1.81% Roof $ 15,000.00 Estimate Mortgage Interest rate 3.25% Payment $1,035.68 Period in years 30 PMI $ 106.69 Taxes $ 377.84 Insurance $ 103.23 Total $2,040.44 Utilities $417 DEAL 2Deal 2 is a commercial property that in a well loved local neighborhood where renovations and flips are very hot.it requires some work to turn it into a duplex but its location is great and architecture very unique.

Each deal is unique.

It's like trying to get advice on dieting, relationships or Covid.

"Too low" is a price that cannot be justified with the facts of the property (including comps, condition, market supply/demand, sellers unique needs, etc), and IMO, should be completely irrelevant to the asking price.If I list my $300k house for $1m tomorrow, because no one can stop me from doing so, would you ever consider offering anything close to that?

While many say Rich Dad, Poor Dad (for very good reason), there are some unique answers that can help you out tremendously. 

Combine that with some great fishing, boating, beaching and just about every store you can think of close by and you have a very unique town.One setback is the city is discussing Single family housing as rentals and their policy given the housing shortage we are in.lots of full time residents have been complaining of the parties and turnover vacation rentals bring into our nice quiet neighborhoods.