I’d recommend starting with resources like Short-Term Rental, Long-Term Wealth by Avery Carl and real estate podcasts like BiggerPockets, connecting with investors in vacation rental groups, and researching reliable management companies in your target areas to make the process as hands-off as possible.

If not feasible, consider increasing rent, reducing purchase price, incorporating future benefits, or targeting multifamily properties.

I joined Bigger Pockets in the hopes to connect with like minded individuals who would like to mentor and or just overall help one another so that everyone can be confident and achieve the best possible outcome as we embark on this Journey of investing. 

Depending on where you are, you might have a different target renter than I do.I have a couple properties we are looking to develop on, I'll send you a PM

Remaining TCPA compliant is such a moving target these days.

Do you have a nice amount saved up for the activities you enjoy(I assume yes given a 30+ year in Tech plus you mentioning making lots of money already in real estate).If that is the case, what are you looking to achieve now within real estate?

One such thing is: not knowing the target buyer.  

One other positive side effect of having leverage on the property is that it is less of a target for a potential lawsuit.At the end of the day it really comes down to your objectives and goals as well as your personal preferences and comfort level.

You can not possibly target who is or who isn't motivated, so DMM, cold calling, anything to do with a list, can't target motivated sellers.But you don't need to be able to target them. 

Here’s the quick-and-dirty lowdown to get you started:1️⃣ Where to Look:LoopNet & Crexi: Good for commercial deals, though the best ones go fast.MLS (Multiple Listing Service): Access through a realtor for hidden gems.Auction Sites: Think Auction.com or HUD homes for distressed properties.Direct Mail Campaigns: Target landlords with older properties (especially those with code violations).2️⃣ Systems for Finding Deals (Step-by-Step):Set Your Criteria: Market, budget, unit count, rehab level.Build a Deal Funnel: Use LoopNet, Crexi, wholesalers, auctions, and brokers.Analyze Quickly: Use a property calculator to see if it cash flows.Direct Outreach: Contact sellers or property managers directly.Get Your Network Tight: Property managers, realtors, contractors—they’ll drop the best leads.3️⃣ What Makes a Good Deal:Cash Flow Positive from Day 1.Below Market Value (usually needs rehab).Upside Potential: Think rent increases, better management, or refinancing options.4️⃣ How to Become the Better/Best:Study the Market Like a Hawk.