We plan on doing a wrap around loan and I like to know what’s the best way to go about this cost effective and secured..

The proper goal of charity is not to give (and virtue signal one's giving) but to see that the gift has some beneficial effect.   

Awesome to hear that you’re thinking about pulling the trigger on a house hack - it’s easily the best financial decision you will ever make if done correctly.A lot of people on BP will tell you that renting by the room is not a sound investment; that you can’t effectively manage multiple strangers in a household; that you’ll relinquish your privacy/sanity/personal space/landlord status etc etc.As someone who lives with 5 roommates (including my wife + 2 dogs) I can tell you that it’s absolutely not the big bad monster that it’s made out to be.Because you have multiple streams of income in a single property, if a tenant flakes, you still have partial coverage of your mortgage payment - not the case in a traditional rental or “luxury” house-hack.

.), I've then effectively freed myself of, depending on the car and student loan, roughly $500-800/month.

Maybe look on Angie’s list or BBB for a smaller roofing company that might bid a more cost effective price. 

For that reason I highly suggest the following books,Rich Dad, Poor DadSecrets of the Millionaire Mind7 Habits of Highly Effective PeopleHow to Win Friends and Influence PeopleThese are all wildly popular books and you should be able to pick them up at your local library. 

What the borrower does is outside your control and has a huge effect on timelines.

I'm a landlord in Ma and I want to put in surveillance cameras with voice recording in common areas/hallways.

When I started investing in RE, negative cash flow would have effected the type of food I could eat (I would not have starved, but a lot more rice and beans than I desire).  

I really won't be limited by my lender much at all, I'm pre-approved for a higher amount that I can afford a down payment for (when also considering closing cost, inspections etc...) even with doing FHA or a low down payment conventional loan.I haven't gotten a credit card yet because I'm just starting to analyze properties and don't want to make any changes that would effect my pre-approval.