We've raised a ton of capital.I feel we need to level up.

You will find different companies providing different levels of service with these four areas.So, it comes down to how much help you need or want.Some companies are down right unscrupulous and are mostly looking to make money off of you (from you). 

Being able to flip in this area now just show's the high levels of appreciation thats been occurring in recent years. 

I guess it's also worth looking at what's happening in the economy on a macro level - energy prices are on the rise (in some regions they are at an all time high already).

They'll look at the experience level of all guarantors in the business. 2 might work, give them a call and see.

It looks like you want to manage it well, but the enterprise level solutions (yardi, appfolio) are too expensive.

Identifying your desired level of effort and risk tolerance helps identify the appropriate investment for you. 

I was wondering how do you build a comfort level to purchase the property? 

I used the use this criteria for high level screening on sites: 600+ credit score, income must be 3 times monthly rent, 2 years of work history, no evictions, must provide at least 1 landlord reference.

Nice neighborhood and high rents.The upper level I was going to be able to increase the rent, just closing a weird second living room it has and convert it into a bedroom.