Plan for the future. Please shoot holes in it!

[Robert Khabbaz]

Hello all, I'm newish to BP, and have done a lot of reading and listening in the last few weeks.  I have been around real estate investing all my life so I'm pretty familiar with most strategies being used.  I always knew I wanted to start investing and building wealth, but have been waiting for my career to jump start and to save some money to start.  

I have a plan and need feedback (good or bad) on it.  I currently have one rental home that is paid for in full (free and clear).  The value of the home is around 50k and it is currently rented for $550 a month.  The rent on this property is lower than it could be and I could easily get $650 for it.  I would love to expand and grow in the next 5 years, hopefully acquiring 8-10 more properties.  I have saved up (for investing purposes) 20k.  My plan is to pull 30k out of my current rental, find other homes in my area with values around 50-60k and pull conventional financing on them putting 20% down.  After doing all the math, my payment with taxes and insurance would be around $340-$360 monthly.  The area that I'm looking at buying in has a median rent of $700-$900 (depending on upgrades, bedrooms, etc..)    

One of my hangups right now is deciding whether to sell the properties on a land contract for a higher price i.e $59,900, $69,900, etc... and getting a 10-20% down payment, or stick to renting them out for $800/monthly.  

I know I have not mentioned any money allocated for repairs/rehabs.  I have thought about this.  Typically at that price range in the areas i'm looking to buy, repairs would be cosmetic (paint,carpet, good cleaning)  I may run into replacing a roof or a furnace, but plan to have money in reserve to take care of those things.  

The land contract idea intrigues me, simply because I will get my initial investment back per DP, and also make 7-10% interest on the money.  I realize the cash flow will be less, but I'm still building equity.  

I plan to save all the cash flow made from investments and re invest into more properties.  Rinse and Repeat! 

I hope I'm heading in the right direction, I'm sure my plan is flawed, but that's what this site is for!    

Thanks, look forward to reading the input!