I intend on sending the tenant a bill for the exact repair cost as "additional rent" (per the lease) instead of evicting in the winter and deducting from the security deposit.

Additionally, his credit is not the best, and he has limited funds for a down payment.Any potential options or solutions that may be available?

Then you can check AirDNA.co (or similar site). 

A new site for NH foreclosure auctions just launched called Bid Pirate, worth investigating.

Additionally, we have equity of approximately $145,000.Now, we are faced with a dilemma: should we sell our current property and purchase in a more favorable neighborhood, or should we rent the house and let it pay for itself.We would greatly appreciate any advice you may have.

In addition, you want a separate bank account for the rental property to separate it from your personal accounts.

Quote from @Zach Howard: Quote from @V.G Jason: Quote from @Zach Howard: @V.G JasonTo someone just starting out (only option of OOS) who can get access to 200k, but no additional financing at this time but an additional 50-100k max in reserve cash, where might you recommend they start - markets/property type/strategy?

Additionally, trying to spot paint even a white wall with white paint doesn't work, let alone other colors.

So you have some great resources right off the bat, my additional Referrals would be too many :)

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.