We've had tenants request such when they were applying for housing assistance or other assistance with their living expenses or educational expenses.

Unless you want to spend the time researching the questions you have I would definitely hire out your accounting and tax work. 

You can leverage family and friendships (willing) to assist in research on city, schools, markets, etc. 

DM me and lets see how I can assist. 

I have a 3 family in Brooklyn grossing 135k a year and I wasn’t spending near those numbers in vacancy and repairs.

I would focus on repairing your credit. see a specialist (faster) or open credit cards little by little and pay them off each month. im not saying increase your spending, just saying instead of buying that tank of gas in cash use a cc and immediately pay it off. while your credit is repairing, start banking cash. build a budget and stick to it. 80K a year is good money, make it a goal of yours to retain as much of it as possible i.e. don't eat out, don't go to the local pub, drive a modest paid off car etc. once your credit is up and savings is up, use the 80k a year plus savings to get leverage. then use that leverage to buy your properties. if your looking for a get rich quick scheme, id advise u skip over RE. don't get me wrong, you can make money fast by flipping homes but you didn't mention having experience in that area so I assume you don't. another option if your really in a hurry is to find a partner with experience and cash, and see if you can buy into one of his/hers deals. you would have to market yourself for this and see what type of skills they may need that you have. maybe you can buy in and use your web development skills to beef up and/or maintain your partners website saving them money on outsourcing. that might be your ticket into a partnership. since you mentioned your helping your friend, maybe you can partner with him?

Hi Gavin, I think the question becomes how much time do you inevitably spend on maintenance and what part is it?

I want to start investing soon, but don't want to regret spending the money on a mastery if the outcome is not what i expected.

However, some of the best agents won't work with buyers who waver too much about buying because they can spend time with other buyers who will actually buy. 

When I   got a mentor  that made all the difference  he was able to help translate the info and assist in setting up a canadian based business that worked for me. and NO I did not need a pile of money to get started just a lot of hard work.