Hello everyone,

I just recently graduated from Rutgers Business School with a degree in Accounting, and I am relatively new to real estate investing. With this post I am really hoping to gain some insight from you guys regarding some of the difficulties and challenges real estate investors face on a day-to-day basis. After speaking with family and peers of mine, they  recommended that I check out the forums on biggerpockets to get a better idea of the thought process of some successful and knowledgeable investors. I am really hoping to kickstart my real estate career and any thoughts or comments would be greatly appreciated!

1) What does buy and hold investing mean to you?

2) Have you had any regrets since getting into real estate investing?

3) Do you recommend hiring a property manager once I begin to invest in more properties? If so, what are some of the things that they take care of for you?

4) What are some of the biggest challenges/headaches that you face self-managing your properties?

Thank you,

Mike S.

@Michael Santiago My quick answers:

1) What does buy and hold investing mean to you? - Buy, till you die, and never sell............unless there is a better opportunity to do so.

2) Have you had any regrets since getting into real estate investing? - No......a million times.....NO

3) Do you recommend hiring a property manager once I begin to invest in more properties? If so, what are some of the things that they take care of for you? - Yes. I want my portfolio to be as passive as possible. The Property Manager (PM) takes care of EVERYTHING and sends you money every month. Your job is to manage your PM. 

4) What are some of the biggest challenges/headaches that you face self-managing your properties? - When I did self manage my first property, it was a just business, not a headache to deal with everything. If there was an issue, I would need to handle it. I often tried to fix things myself (I'm a bit handy) but if I couldn't or didn't have time, I would hire out. 

1) What does buy and hold investing mean to you?

Buy based on cash flow first and appreciation second. Hold the investment to replace income during "working" years and sell to live our "retirement". In parentheses because I'm hoping the cash flow provides a sort of retirement before I get to social security retirement age.   

2) Have you had any regrets since getting into real estate investing?

Not getting involved in the industry sooner. Not moving as quickly as I should on the house right next door to me and seeing someone else scoop it up. At least I know the guy that got it will do a good job with it (@Alex Deacon ). That taught me a valuable lesson though that if you see a good deal you should do everything you can to find ways to fund it.  

3) Do you recommend hiring a property manager once I begin to invest in more properties? If so, what are some of the things that they take care of for you?

Depends if you invest in your backyard or from afar. Also, depends on your personal preference. I think it's valuable to do it yourself at least once because then you know what goes into managing a property. 

4) What are some of the biggest challenges/headaches that you face self-managing your properties?

I luckily have not had to evict or move through that process yet because I've screened well/got lucky, but once that happens I'm sure the first time will be stressful. I think that the biggest thing I've learned so far is that the first time handling everything is kind of a headache/challenge, but after that it's not so bad. I think that after I took on a property that needed some more serious repairs I became a bit more blunted to $1000+ repair bills. That taught me the importance of a reserve fund and actually saving your money for repairs. If you're in a good place financially and buy right to account for the unexpected you won't be as stressed about it.