Right now I'm just looking at properties all over the place learning how to analyze a property etc but as somebody that is looking to make their first investment, i want to avoid if possible the extra outlays that can potentially come with an older house. 

Investors at this time should be extra careful

You might find that they could charge enough extra rent to pay for themselves.

(Just don't tell your lender that you are going to do that) The umbrella policy is an extra layer.

It makes the dialogue more between the two members rather than with the whole membership (unless you take extra steps to click on every triangle).

So, it's not like Scott had devised some extra default prone strategy to troll gullible fools, while making all his money teaching noobs to self-destruct.

How certain of the appreciation are you would also play into that question.Run some scenarios on what you could do with the extra cash vs what you stand to gain from the appreciation play and decide based on that and your goals.

Im at base pay since I Just started, top pay at this job is at 5 years and we make 100k base pay, there are guys easily clearing 160k due to OT and other extra money functions. we also have a lot of opportunity to move up in position, Supervisors clear 230k like nothing so right now I'm not making much but long term this is one of the best city jobs to work.

So if you want to handle the extra work, like cleaning, repairs and all of the calls and texts, then go for it.

So as investing partners it makes sense because we will both have extra cash at the same time, we partner up to cut the risk in half + we both specialize in a couple things the other does not in terms of being a rental property owner (e.g. running the books + marketing vs actually fixing things).