Their biggest problems are things like:“my net worth is $10M and $8.5M of it is in my three properties I purchased 25 years ago.

I agree that the swarms of "my market is great, contact me for more info" tends to be the biggest problem but a lot of that will depend on you, the poster - as @Russell Brazil mentioned just hit the report button on posts and we can check them out faster. 

It's the biggest feeder city there is besides NYC and also one of the most glamorized tourist spots in recent years. 

However, in this case it’s worth circling back in 3 months, 6 months, or a year because this seller wants to sell, he’s just not ready to give up his fantasy deal.If the seller’s response is acceptance of the outline of my offer but countering on price or terms, it may be worth negotiating because we MAY be able to get to YES.My biggest profits have occurred when I made offers that were nowhere near what the seller was asking and yet WERE ACCEPTED, or with small modifications. 

Buildium can accommodate under 50 units and I know companies that use it for 600 units.Appfolio has a 50 unit minimum and it is the biggest player in SFR and small multifamily PM software.

I also BELIEVE their biggest concern is tax liability shifting.

.: What are the 5 biggest mistakes seasoned investors are making here in the forums? 

The biggest issue that came with this method is that it still works great for VRBO, but now after an AirBnb booking I have to ask the guest for their email to get this process started.Zapier is also monitoring for the returned signed RA and that point then sends out all the info the guests needs for their stay.The rest of the email automation is handled by the PMS.My biggest pain, is when I get a difficult guest, or when things break mid stay.

(option B)My biggest question is not able to decide between option A vs option B.If i go with option A tenants can manage that area well using their own landscapers every once in 2 weeks like that.

Biggest issue would be financing and, of course, you wouldn't get to take advantage of appreciation.