I also am planning to meet with my PM on Monday to discuss pain points and better expectations, I would love to hear what sort of expectations you set with property managers?

“Please, Learn from My Pain”)Leases: Month-to-Month MagicStrangers are like boxes of chocolates—you never know when one’s going to melt all over your sofa.

Simple does NOT mean "easy" or pain free. 

I’m working on scaling my multifamily portfolio as well, and I’m always looking for sharp, motivated people to collaborate with.

Unfortunately, most PMC contracts are pretty vague making it a challenge to get useful information.3) A mix of the two aboveSome PMCs have internal handyman type ServiceTechs for small jobs that they bill hourly for, but get bids for any job requiring a licensed contractor.An owner should understand what type(s) of the above that their PMC uses and discuss as necessary to better understand.THE CHALLENGES OF GETTING 3 BIDSWe wanted to touch on this topic because it seems to be a pain point between PMCs and owners.In theory, it's easy to get multiple bids - you just search online for companies and contact them to get a bid. 

However, Austin proper has a high barrier to entry due to the sharp rise in property values in recent years.

Having a healthy fear going into any deal can keep your sense sharp to avoid potential pitfalls. 

Quote from @Nate Sanow: Yes I own two that are near 100 years old and I will tell you they are a pain in the you know what compared to all of my post WW2 properties especially post 1980… layouts are better in the last 50 years and energy efficiency is better and I can keep going… HOWEVER to reply to the other aspect of your question, I’ve found appreciation is better with older properties in areas of the path of progress.

Did they previous take on bridge debt and has that caused them undo "pain" in the recent years?

At that time, i will have the knowledge and network to expand and build my portfolio at an increasing speed and then it will be part of my growing pains for my business.I will most likely have that CPA do my returns for the real estate and then have my Tax Accountant still do my Personal, helps with Checks and Balance and cost savings.Do you have cost segregation, or anything like that on any of your properties?