I have traditionally chosen the lowest deductible and pay a higher premium monthly for this, but I wonder if I'm leaving money on the table.

the only way not to do that is to spend time in your chosen market in person, have patience, and potentially wait years like i said for that payoff.if you're willing, go to your chosen market every month in person to look at properties, build your team, get to know different neighborhoods, go to REIA meetings, etc. 

@Eric TeranGiven that you are limited in your ability to convert your condos to a medium-long term strategy and have chosen to not do so with your VA basement, how are you faring?

San Fran, San Diego, LA, NYC, Miami) who have chosen to invest in some of these other markets. 

I've chosen Jacksonville as my next market to invest rental Property.My main question, as a remote investor, is how can I find the Off market deals?

I'd say first identify a strategy and establish your Core 4.The main challenge I observed is that individuals often lack a clear end goal or strategy, or they select a market that doesn't align with their chosen strategy.

FAST FORWARD 10 YEARS.. 2027...the 2 'buy and hold' single family homes you bought will have more than doubled in value and your carefully chosen SMALL local in your backyard commercial project will be a successful part of the community and YOUR business relationships will have introduced you TO SO MANY MORE OPPORTUNITIES.Knowing this... which path will give YOU AND YOUR FAMILY the best quality of life and really get you to the best place in 2027?

This camp is using the benefit of hindsight to project how their financial future might have been had they chosen a different path.Beyond that, anyone making a blanket statement that college is a waste of time and money should be dismissed immediately as uninformed or with some specific motive or angle.

I have chosen the Cleveland area as I would like to purchase something near where a friend has bought his apartment complex.

Narrow your goal so you can become very comfortable with the niche you have chosen.