I also don't want to trade one stressful job for another when I'm ultimately working for freedom. 

there are lots of them - you need to find them.you should also, if you can, go to Cleveland and meet folks in person.and i think @Travis Timmons said it - but even if you find trustworthy folks and they make good recommendations, everything is still ultimately going to be your responsibility. 

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

This is a great topic of discussion and ultimately I think depends on your goals and what metrics you personally try to maximize. 

depends on the quality of the assets and the reliability of consistent rental income.this is an age old argument and really a personal choice at the end of the day.

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

Time to build the legacy.Check out the Start Here page http://www.biggerpockets.com/starthereCheck out BiggerPockets Ultimate Beginner's Guide - A fantastic free book that walks through many of the key topics of real estate investing.Check out the free BiggerPockets Podcast - A weekly podcast with interviews and a ton of great advice.

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

I read your post from several years back - ”The Ultimate Guild to Grading……” very informative, and I’m assuming most of the insights still holds true +/- market changes on price points -   

I'm local and definitely can see how that is a tough choice with the location.If it was by the numbers I'd say spend the money to make it worth as much as possible and try to sell, then use the profits to fund what you want to do next.